WO2015007564A1 - Substituted n-(1,2,4-triazol-3-yl)arylcarboxamide compounds and their use as herbicides - Google Patents

Substituted n-(1,2,4-triazol-3-yl)arylcarboxamide compounds and their use as herbicides Download PDF

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Publication number
WO2015007564A1
WO2015007564A1 PCT/EP2014/064531 EP2014064531W WO2015007564A1 WO 2015007564 A1 WO2015007564 A1 WO 2015007564A1 EP 2014064531 W EP2014064531 W EP 2014064531W WO 2015007564 A1 WO2015007564 A1 WO 2015007564A1
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Prior art keywords
alkyl
alkoxy
group
haloalkyl
methyl
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PCT/EP2014/064531
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French (fr)
Inventor
Frederick CALO
Markus Kordes
Helmut Kraus
Thomas Mietzner
Thomas Seitz
Klaus Kreuz
Maciej Pasternak
Trevor William Newton
Dario MASSA
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Basf Se
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Priority to EP14735988.9A priority Critical patent/EP3022190B1/en
Priority to US14/905,056 priority patent/US9926284B2/en
Priority to CN201480040249.3A priority patent/CN105377836B/en
Priority to BR112015029979A priority patent/BR112015029979A2/en
Publication of WO2015007564A1 publication Critical patent/WO2015007564A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to substituted N-(1 ,2,4-triazol-3-yl)arylcarboxamide compounds and the N-oxides and salts thereof and to compositions comprising the same.
  • the invention also relates to the use of the N-(1 ,2,4-triazol-3-yl)arylcarboxamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation.
  • the invention relates to methods of applying such compounds.
  • WO 2012/028579 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 3- and 4-positions of the aryl ring and their use as herbi- cides.
  • WO2013/087577 describes certain N-(tetrazol-4-yl) and N-(triazol-3-yl)arylcarboxylic acid amides, which additionally carry a substituent on the benzamide nitrogen and their use as herbicides.
  • WO2013/144234 also discloses 1 ,2,4-triazole derivatives as herbicides.
  • the compounds of the prior art often suffer form insufficient herbicidal activity in particular at low application rates and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.
  • N-(1 ,2,4-triazol-3- yl)arylcarboxamide compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and/or a high compatibility with crop plants.
  • the N-(1 ,2,4-triazol-3-yl)arylcarboxamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.
  • R 1 is selected from the group consisting of cyano-Z 1 , halogen, nitro, d-Cs-alkyl, C2-C8- alkenyl, C2-C8-alkynyl, C3-Cio-cycloalkyl-Z 1 , C-i-Cs-haloalkyl, C2-C8-haloalkenyl, C3- Cs-haloalkynyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Z 1 , Ci-C 4 -alkylthio-Ci-C 4 -alkyl, Ci-C 4 -alkylthio-Ci-C 4 -alkylthio-Z 1 , C 2 -C 6 -alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-
  • X is N or CR 2 ;
  • R 2 , R 3 are identical or different and independently selected from the group consisting of hydrogen, halogen, OH-Z 2 , NO2-Z 2 , cyano-Z 2 , Ci-C6-alkyl, C2-Cs-alkenyl, C2-C8- alkynyl, C3-Cio-cycloalkyl-Z 2 , C3-Cio-cycloalkoxy-Z 2 , where the C3-Cio-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, Cs-Cs-haloalkynyl, d-Cs-alkoxy- Z 2 , Ci-Cs-haloalkoxy-Z 2 , C3-Cio-cycloalkyl- Ci-C2-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy
  • R 2 and R 3 together form a saturated 5- or 6-membered ring, optionally containing an oxygen or a S(0) n heteroatom, the 5- or 6-membered ring being unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy;
  • R 4 is selected from the group consisting of hydrogen, cyano- Z 1 , halogen, nitro, Ci-Cs- alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci- C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z 1 , Ci-C4-alkylthio-Ci
  • R 5 is selected from the group consisting of cyano- Z 1 , halogen, nitro, Ci-Cs-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino,
  • R 6 is selected from the group consisting of hydrogen, CN, nitro, hydroxy, amino, C1-C6- alkyl, Ci-C6-cya no-alky I, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or par- tially or completely halogenated, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylcarbonyl,
  • heterocyclyl is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups R', which are identical or different;
  • R 7 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy, Ci- C4-alkoxy-Ci-C4-alkyl and Ci-C4-haloalkoxy-Ci-C4-alkyl; n is 0, 1 or 2; k is 0, 1 or 2;
  • R', R 11 , R 21 independently of each other are selected from the group consisting of
  • Z, Z 1 , Z 2 independently of each other are selected from the group consisting of a
  • Z 2a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-
  • Ci-C4-alkanediyl Ci-C4-alkanediyl-0 and
  • R b , R 1b , R 2b independently of each other are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-
  • heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R c , R 2c independently of each other are selected from the group consisting of
  • Ci-C6-alkyl C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstitute
  • R d , R 2d independently of each other are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl
  • Ci-C6-alkyl C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalk
  • R e , R f together with the nitrogen atom, to which they are bound may form a 5-, 6 or
  • N-bound heterocyclic radical which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R 2e , R 2f independently of each other have the meanings given for R e , R f ;
  • R9 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, C1-C4- alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen
  • R9, R h together with the nitrogen atom, to which they are bound may form a 5-, 6 or
  • R k has the meanings given for R c ; an N-oxide or an agriculturally suitable salt thereof.
  • the compounds of the present invention i.e. the compounds of formula I, their N-oxides, or their salts are particularly useful for controlling unwanted vegetation. Therefore, the invention also relates to the use of a compound of the present invention, an N-oxide or a salt thereof or of a composition comprising at least one compound of the invention, an N-oxide or an agricultural- ly suitable salt thereof for combating or controlling unwanted vegetation.
  • the invention also relates to a composition comprising at least one compound according to the invention, including an N-oxide or a salt thereof, and at least one auxiliary.
  • the invention relates to an agricultural composition comprising at least one compound according to the invention including an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary customary for crop protection formulations.
  • the present invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound according to the invention, including an N-oxide or a salt thereof, to act on unwanted plants, their seed and/or their habitat.
  • the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures.
  • Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the compounds of formula I may be present in the form of their tautomers.
  • the invention also relates to the tautomers of the formula I and the stereoisomers, salts and N-oxides of said tautomers.
  • N-oxide includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N-oxides in compounds of formula I can in particular be prepared by oxidizing the ring nitrogen atom(s) of the N-(1 ,2,4-triazol- 3-yl)arylcarboxamide ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides, or the ring nitrogen atom(s) of a heterocyclic substituent R, R 1 , R 2 or R 3 .
  • the present invention moreover relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably nonradioactive isotope (e.g., hydrogen by deuterium, 12 C by 13 C, 14 N by 15 N, 16 0 by 18 0) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom.
  • the compounds according to the invention contain more of the respective isotope than this naturally occurs and thus is anyway present in the compounds of formula I.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of formula I, their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • Useful agriculturally suitable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, C1-C4- hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isoprop- ylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetrame- thylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensul- fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • weeds undesired vegetation
  • weeds are understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any).
  • Weeds, in the broadest sense, are plants considered undesirable in a particular location.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n - Cm indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
  • partially or completely halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • a partially or completely halogenated radical is termed below also “halo-radical”.
  • partially or completely halogenated alkyl is also termed haloalkyl.
  • alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 car- bon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
  • Ci-C4-alkyl examples include methyl, ethyl, n-propyl, iso-propyl, n- butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl.
  • Ci-C6-alkyl are, apart those mentioned for Ci-C4-alkyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylbut
  • Ci-Cio-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2- methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1 -ethylpentyl, 2-ethylpentyl, 3- ethylpentyl, n-octyl, 1 -methyloctyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propylpentyl, 2-propylpentyl, nonyl, decyl, 2-propylheptyl and 3-propylheptyl.
  • alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • haloalkyl as used herein (and in the haloalkyl moieties of other groups com- prising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms (“Ci-Cs-haloalkyl”), frequently from 1 to 6 carbon atoms (“C1-C6- haloalkyl”), more frequently 1 to 4 carbon atoms (“Ci-C4-haloalkyl”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.
  • haloalkyl as used herein (and in the haloalkyl moieties of other groups com- prising a haloalkyl group,
  • haloalkyl moie- ties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halomethyl, in particular from Ci-C2-fluoroalkyl.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • Ci-C2-fluoroalkyl examples include fluo- romethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, pentafluoroethyl, and the like.
  • Ci-C2-haloalkyl are, apart those mentioned for Ci-C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 2-chloroethyl, 2,2,- dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 1 -bromoethyl, and the like.
  • Ci-C4-haloalkyl are, apart those mentioned for Ci-C2-haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trif I uoroprop-2-yl , 3-chloropropyl, 4-chlorobutyl and the like.
  • cycloalkyi as used herein (and in the cycloalkyi moieties of other groups com- prising a cycloalkyi group, e.g. cycloalkoxy and cycloalkylalkyi) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C3-Cio-cycloalkyl”), preferably 3 to 7 carbon atoms (“C3-C7-cycloalkyl”) or in particular 3 to 6 carbon atoms (“C3-C6- cycloalkyl").
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • halocycloalkyl as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are
  • cycloalkyl-alkyl used herein denotes a cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkylene group.
  • C3-C7- cycloalkyl-Ci-C4-alkyl refers to a C3-C7-cycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Examples are cyclo- propylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobu- tylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclo- hexylethyl, cyclohexylpropyl, and the like.
  • alkenyl denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 (“C2-C8-alkenyl”), preferably 2 to 6 carbon atoms (“C2-C6-alkenyl”), in particular 2 to 4 carbon atoms (“C2-C4-alkenyl”), and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 - methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 - methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl, 1 -methylethenyl,
  • haloalkenyl as used herein, which may also be expressed as "alkenyl which is substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 ("C2-C8-haloalkenyl") or 2 to 6 (“C2-C6-haloalkenyl”) or 2 to 4 (“C2-C4-haloalkenyl”) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
  • alkynyl denotes unsaturated straight-chain or branched hydro- carbon radicals having usually 2 to 8 (“C2-C8-alkynyl”), frequently 2 to 6 (“C2-C6-alkynyl”), preferably 2 to 4 carbon atoms (“C2-C4-alkynyl”) and a triple bond in any position, for example C2- C4-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl,
  • haloalkynyl as used herein, which is also expressed as “alkynyl which is substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 carbon atoms (“C2-C8-haloalkynyl”), frequently 2 to 6 (“C2-C6-haloalkynyl”), preferabyl 2 to 4 carbon atoms (“C2-C4-haloalkynyl”), and a triple bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • C2-C8-haloalkynyl unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 carbon atoms
  • C2-C6-haloalkynyl frequently 2 to 6
  • C2-C4-haloalkynyl preferabyl 2 to 4 carbon atoms
  • alkoxy denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms ("d-Cs-alkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-alkoxy”), preferably 1 to 4 carbon atoms (“Ci-C4-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • C1-C4- Alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy,
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1
  • haloalkoxy denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms (“Ci-Cs-haloalkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-haloalkoxy”), preferably 1 to 4 carbon atoms (“C1-C4- haloalkoxy”), more preferably 1 to 3 carbon atoms (“Ci-C3-haloalkoxy”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
  • Ci-C 2 -Haloalkoxy is, for example, OCH 2 F, OCH F 2 , OCF 3 , OCH 2 CI, OCHC , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5.
  • Ci-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH 2 F)-2-fluoroethoxy, 1 -(CH 2 CI)-2-chloroethoxy, 1 -(CH 2 Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
  • alkoxyalkyl denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Ci-C6-alkoxy-Ci-C6-alkyl is a Ci-C6-alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above.
  • Examples are CH2OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (l -methylpropoxy)-methyl, (2- methylpropoxy)methyl, CH2-OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2- (1 -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1 - methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1 -methylpropoxy)-propyl, 2-(2-methylprop
  • haloalkoxy-alkyl denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Examples are fluoromethoxymethyl, difluoro- methoxymethyl, trifluoromethoxymethyl, 1 -fluoroethoxymethyl, 2-fluoroethoxymethyl, 1 ,1 - difluoroethoxymethyl, 1 ,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1 ,1 ,2- trifluoroethoxymethyl, 1 ,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethox- ymethyl, 1 -fluoroethoxy-1 -ethyl, 2-fluoroethoxy-1 -ethyl, 1 ,1 -difluoroethoxy-1 -ethyl, 1 ,2- difluoroethoxy-1 -ethyl, 2,2-difluoroethoxy-1 -ethyl, 1 ,1 ,2-trifluoroethoxy-1 -e
  • alkylthio (also alkylsulfanyl, “alkyl-S” or “alkyl-S(0) k “ (wherein k is 0)) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms (“Ci-Cs-alkylthio”), frequently comprising 1 to 6 carbon atoms (“Ci-C6-alkylthio”), preferably 1 to 4 carbon atoms (“Ci-C4-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C4-Alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (iso- propylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 - dimethylethylthio (tert-butylthio).
  • Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 - methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
  • Ci-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • haloalkylthio refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine.
  • Ci-C 2 -Haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHCI 2 , SCC , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2- fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2
  • Ci-C4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,
  • Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
  • alkylsulfinyl and “alkyl-S(0)k” (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • alkylsulfinyl and “alkyl-S(0)k” (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -alkylsulfinyl refers to a Ci-C 2 -alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-alkylsulfinyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • Ci-C4-alkylsulfinyl is additionally, for example, n-propylsulfinyl,
  • C1-C6- alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2- methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl,
  • alkylsulfonyl and “alkyl-S(0)k” (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-alkylsulfonyl refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C4-alkylsulfonyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C6-alkylsulfonyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-alkylsulfonyl is methyl- sulfonyl or ethylsulfonyl.
  • Ci-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec- butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert- butylsulfonyl).
  • Ci-C6-alkylsulfonyl is additionally, for example, pentylsulfonyl,
  • alkylamino denotes in each case a group R * HN-, wherein R * is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms ("Ci-Ce- alkylamino"), preferably 1 to 4 carbon atoms("Ci-C4-alkylamino").
  • Ci-C6-alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso- butylamino, tert-butylamino, and the like.
  • dialkylamino denotes in each case a group R * R°N-, wherein R * and R°, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms ("di-(Ci-C6-alkyl)-amino"), preferably 1 to 4 carbon atoms (“di- (Ci-C4-alkyl)-amino").
  • Examples of a di-(Ci-C6-alkyl)-amino group are dimethylamino, diethyla- mino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl- isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl- isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.
  • aryl as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.
  • heteroaryl refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrim- idyl and the like.
  • N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO2.
  • An unsaturated heterocycle contains at least one C-C and/or C-N and/or N-N double bond(s).
  • a fully unsaturated heterocycle contains as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the size(s) of the ring(s).
  • An aromatic monocyclic heterocycle is a fully unsaturated 5- or 6-membered monocyclic heterocycle.
  • An aromatic bicyclic heterocycle is an 8-, 9- or 10-membered bicyclic heterocycle consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring.
  • the heterocycle may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle include:
  • oxirane-2-yl aziridine-1 -yl, aziridine-2-yl, oxetan-2-yl, azetidine-1 -yl, azetidine-2-yl, azetidine-3- yl, thietane-1 -yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahy- drothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1 -yl, imidazolidin-2-yl, imidazo
  • Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3- yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2- isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isox
  • a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring is e.g. a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring.
  • Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3- pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,
  • 6- membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, ben- zimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, iso- chinolinyl, purinyl, 1 ,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.
  • Preferred compounds according to the invention are compounds of formula I or a stereoisomer, salt or N-oxide thereof, wherein the salt is an agriculturally suitable salt. Further preferred compounds according to the invention are compounds of formula I or an N-oxide or salt thereof, especially an agriculturally suitable salt. Particularly preferred compounds according to the invention are compounds of formula I or a salt thereof, especially an agriculturally suitable salt thereof.
  • variable X in the compounds of formula I is CR 2 .
  • Preferred compounds according to the invention are compounds of formula I, wherein R 1 is selected from the group consisting of CN, halogen, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z 1 , Ci-C4-alkylthio-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkylthio-Z 1 , C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, C1-C4- halo
  • R 1 is selected from halogen, CN, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Ci-C 4 -alkyl, Ci-C 4 -alkylthio-Ci-C 4 -alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C4-haloalkoxy, C3-C4-alkenyloxy, C3-C4-alkynyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- haloalkoxy-
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C3-C6- cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, specifically R 1 is F, CI, Br, N0 2 , CH 3 , cyclopropyl, CF 3 , OCH 3 , OCF 3 , SCF 3 , SO2CH3, CH2OCH3 or CH2OCH2CH2OCH3, and more specifically R 1 is CI, N0 2 , CH 3 , cyclopropyl, CF 3
  • variable R 2 of the compounds of formula I has any one of the meanings given above for R 2 with the exception of hydrogen.
  • variable R 2 in the compounds of formula I is a 5- or 6-membered heterocyclyl, where heterocyclyl is a saturated, partially unsaturated or aromatic heterocyclic radical, which contains as ring member 1 heteroatom selected from the group consisting of O, N and S and 0, 1 , 2 or 3 further nitrogen atom(s), where hetero- cyclyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 , as defined herein, which are identical or different.
  • variable R 2 in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from the group consisting of isoxazolinyl (4,5-dihydroisoxazolyl), 1 ,2-dihydrotetrazolonyl, 1 ,4-dihydrotetrazolonyl, tetrahy- drofuryl, dioxolanyl, piperidinyl, morpholinyl, piperazinyl, isoxazolyl, pyrazolyl, thiazolyl, oxazolyl, furyl, pyridinyl, pyrimidinyl and pyrazinyl, where heterocyclyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 which are identical or different and are selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci
  • variable R 2 in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from 4,5-dihydroisoxazol-3-yl, which is unsubstituted or substituted in position 5 with CH3, CH2F or CHF2, 4,5-dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH3, OCH3, CH2OCH3, CH2SCH3, 1 - methyl-5-oxo-1 ,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5-dihydrotetrazol-1 -yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3-methyl-isoxazol-5-yl, 1 -methyl-1 H-pyrazol- 3-yl, 2-methyl-2H-pyrazol-3-yl and
  • variable R 2 in the compounds of formula I is phenyl-Z 2a , where Z 2a is as defined herein, and where phenyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 which are identical or different and as defined above and which are in particular selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci- C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy, and preferably from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkyl and Ci-C2-alkoxy-Ci-C2-alkoxy.
  • variable R 2 in the compounds of formula I is a radical of the following formula:
  • R P1 is hydrogen or halogen, preferably hydrogen, CI, Br or F, and in particular H or F;
  • R P2 is hydrogen, halogen or Ci-C2-alkoxy, preferably hydrogen, CI, Br, F, OCH3 or OCH2CH3, and in particular H, F, CI or OCH3;
  • R P3 is hydrogen, halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-alkoxy-Ci-C2- alkoxy, preferably hydrogen, CI, Br, F, CH 3 , C 2 H 5 , CF 3 , CHF 2 , CH 2 F, CCI 2 F, CF 2 CI, CH2CF3, CH2CHF2, CF2CF3, OCH3, OCH2CH3, OCH2OCH3, OCH2CH2OCH2CH3,
  • variable R 2 in the compounds of formula I is phenyl which is unsubstituted or carries one radical R 21 , where R 21 is preferably at- tached to position 4 of the phenyl group and is as defined above and in particular selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkyl and Ci-C2-alkoxy-Ci-C2-alkoxy, preferably form CH3, C 2 H 5 , OCH3, OC 2 H 5 , CHF 2 , CF 3 , OCH2OCH3 and OCH 2 CH 2 OCH 3 , and specifically from OCH 3
  • variable R 2 in the compounds of formula I is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be un
  • variable R 2 in the compounds of formula I is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6- haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkyl-S(0)k and C1-C4- haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and iso
  • variable R 2 in the compounds of formula I is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C4-alkoxy- Ci-C 4 -alkyl, Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 4 -alkoxy, C1-C4- haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radical
  • variable R 2 in the compounds of formula I is selected from the group consisting of hydrogen, 4,5-dihydroisoxazol- 3-yl, which is unsubstituted or substituted in position 5 with CH3, CH2F or CHF2, 4,5- dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH3, OCH3, CH2OCH3, CH2SCH3, 1 -methyl-5-oxo-1 ,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5- dihydrotetrazol-1 -yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3- methyl-isoxazol-5-yl, 1 -methyl-1 H-pyrazol-3-yl, 2-methyl-2H-pyrazol-3-yl, thiazol-2-
  • Preferred compounds according to the invention are compounds of formula I, wherein R 3 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C4-alkenyloxy, C3- C4-alkynyloxy or R 2b -S(0)k, where the variables k and R 2b have one of the herein defined meanings.
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C 4 -alkyl-S(0) 2 and Ci-C 4 -haloalkyl-S(0) 2 .
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-
  • Ci-C2-haloalkyl Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkylthio, Ci-C2-haloalkylthio, Ci-C 2 -alkyl-S(0) 2 , specifically from H, CI, F, CN, N0 2 , CH 3 , CF 3 , CHF 2 , OCH3, OCF3, OCHF2, SCH 3 , SCF 3 , SCHF 2 , S(0) 2 CH 3 and S(0) 2 CH 2 CH 3 , and more specifically from H, CI, F, CN, CH 3 , CF 3 and S(0) 2 CH 3 .
  • Preferred compounds according to the invention are compounds of formula I, wherein R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl and C1-C2- haloalkyl, in particular from the group consisting of hydrogen, CHF2, CF3, CN, NO2, CH3 and halogen, and specifically from hydrogen, CHF2, CF3, CN, NO2, CH3, CI, Br and F.
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl and C1-C2- haloalkyl, in particular from the group consisting of hydrogen, CHF2, CF3, CN, NO2, CH3 and halogen, and specifically from hydrogen, CHF2, CF3, CN, NO2, CH3, CI, Br and F.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 5 is selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, and in particular from the group consisting of CHF2, CF3 and halogen.
  • R 5 is chlorine or fluorine.
  • R 6 in the compounds formula I is hydrogen.
  • R c is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R d is Ci-C 4 -alkyl
  • R e is hydrogen or Ci-C4-alkyl
  • R f is hydrogen or Ci-C4-alkyl
  • R e , R f together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7- membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 methyl groups,
  • R k is Ci-C 4 -alkyl.
  • R 6 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl-Z and where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups R', which are identical or different.
  • Particularly preferred compounds according to the invention are compounds of formula I, wherein R 6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci-C2-alkyl, particularly from hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2- ynyl, methoxycarbonylmethyl and benzyl.
  • R 6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci
  • R 6 is selected from the group consisting of hydrogen and Ci-C4-alkyl, particularly from hydro- gen, methyl and ethyl.
  • R c is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R d is Ci-C 4 -alkyl
  • R e is hydrogen or Ci-C 4 -alkyl
  • R f is hydrogen or Ci-C 4 -alkyl
  • R e , R f together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7- membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 methyl groups,
  • R k is Ci-C 4 -alkyl.
  • R 7 is selected from the group consisting of Ci-C 4 -alkyl, C3-C7-cycloalkyl, Ci-C 4 -haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C 4 -alkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl.
  • Particularly preferred compounds according to the invention are compounds of formula I, wherein R 7 is selected from the group consisting of Ci-C 4 -alkyl, Ci-C 4 -alkoxy and Ci-C2-alkoxy- Ci-C2-alkyl, particularly from methyl, ethyl, methoxy, ethoxy, n-propyl, methoxymethyl, ethox- ymethyl and methoxyethyl.
  • Most preferred compounds according to the invention are compounds of formula I, where- in R 7 is selected from the group consisting methyl, ethyl, n-propyl and methoxyethyl.
  • R', R 11 , R 21 independently of each other are selected from halogen, Ci-C 4 -alkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C1-C4- alkylthio-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy and Ci-C6-haloalkyloxy, more preferably from halogen, Ci-C 4 -alkyl, C3-C6-cycloalkyl, Ci-C 4 -haloalkyl and Ci-C 4 -alkoxy.
  • R', R 11 , R 21 independently of each other are selected from the group con- sisting of halogen, Ci-C 4 -alkyl, C3-C6-cycloalkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci- C 4 -alkyl, Ci-C 4 -alkylthio-Ci-C 4 -alkyl and Ci-C 4 -alkoxy-Ci-C 4 -alkoxy; in particular selected from halogen, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl and Ci-C 4 -alkoxy- Ci-C 4 -alkoxy; and specifically from CI, F, Br, methyl, ethyl, methoxy and trifluoromethyl.
  • Z, Z 1 , Z 2 independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.
  • Z 2a is selected from a covalent bond, Ci-C2-alkanediyl, 0-Ci-C2-alkanediyl, C1-C2- alkanediyl-0 and Ci-C2-alkanediyl-0-Ci-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyI, O-ethanediyI, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.
  • R b , R 1b , R 2b independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl,
  • Ci-C6-haloalkyl C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy.
  • R b ,R 1b , R 2b independently of each other are selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
  • R b , R 1b , R 2b independently of each other are selected from Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • R c , R 2c , R k independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the
  • R c , R 2c , R k independently of each other are selected from hydrogen, Ci-
  • C4-alkyl Ci-C4-haloalkyl, C2-C-alkenyl, C2-C-haloalkenyl, C2-C-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
  • R c , R 2c , R k independently of each other are selected from hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • R d , R 2d independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.
  • R d , R 2d independently of each other are selected from Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6- cycloalkyl.
  • R e , R f , R 2e , R 2f independently of each other are selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl and Ci-C4-alkoxy, or R e and R f or R 2e and R 2f together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or uns
  • R e , R f , R 2e , R 2f independently of each other are selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and benzyl, or R e and R f or R 2e and R 2f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N- bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R e , R f , R 2e , R 2f independently of each other are selected from hydrogen and Ci-C4-alkyl, or R e and R f or R 2e and R 2f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.
  • R9, R3 ⁇ 4 independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl and benzyl.
  • R3 ⁇ 4 independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl.
  • R h , R 2h independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl; or
  • R9 and R h or R3 ⁇ 4 and R 2h together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is
  • unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of 0, halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and Ci-C4-alkoxy;
  • R h or R3 ⁇ 4 and R 2h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl;
  • n and k independently of each other are 0 or 2, and in particular 2.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, in particular from F, CI, Br, NO2,
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and C1-C4- alkylsulfonyl, in particular from H, CI, F, CN, N0 2 , CH 3 , CF 3 , CHF 2 , OCH 3 , OCF 3 , OCHF 2 , SCH 3 , SCF 3 , SCHF 2 , S(0) 2 CH 3 and S(0) 2 CH 2 CH 3 .
  • R 1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci-
  • Ci-C4-alkoxy-Ci-C4-alkyl Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C 4 -alkyl-S(0) 2 ;
  • R 2 is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci- C4-alkoxy, Ci-C 3 -alkoxy-Ci-C 3 -alkoxy, Ci-C4-haloalkoxy, C 3 -C6-alkenyloxy, C 3 -C6- alkynyloxy, C 3 -C6-haloalkenyloxy, C 3 -C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci- C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxa- zolinyl, where the
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and
  • R 4 is selected from the group consisting of hydrogen and halogen;
  • R 5 is selected from the group consisting of halogen, CHF2 and CF3;
  • R 6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci- C 2 -alkyl;
  • R 7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy-
  • Ci-C 2 -alkyl Ci-C 2 -alkyl
  • R 1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C 4 -alkyl-S(0) 2 ;
  • R 2 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C2- alkoxy-Ci-C 2 -alkyl, Ci-C 2 -haloalkoxy-Ci-C 2 -alkyl, Ci-C 4 -alkyl-S(0) k , where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be un- substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl;
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and Ci-C 4 -alkyl-S(0) 2 ;
  • R 4 is selected from the group consisting of hydrogen and halogen
  • R 5 is selected from the group consisting of halogen, CHF2 and CF3;
  • R 6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci-
  • R 7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy-
  • Ci-C 2 -alkyl Ci-C 2 -alkyl
  • R 1 is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl;
  • R 2 is selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methylsulfonyl, methylsulfinyl, methylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 5- isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5-isoxazolyl;
  • R 3 is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl;
  • R 4 is selected from the group consisting of hydrogen, chlorine and fluorine
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl;
  • R 7 is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxyme- thyl, methoxyethyl and ethoxymethyl;
  • R 1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci-
  • C4-haloalkyl Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and
  • Ci-C 4 -alkyl-S(0) 2 Ci-C 4 -alkyl-S(0) 2 ;
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and Ci-C 4 -alkyl-S(0) 2 ;
  • R 4 is selected from the group consisting of hydrogen and halogen
  • R 5 is selected from the group consisting of halogen, CHF2 and CF3;
  • R 6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci- C 2 -alkyl;
  • R 7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy- Ci-C 2 -alkyl.
  • R 1 is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl;
  • R 3 is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl;
  • R 4 is selected from the group consisting of hydrogen, chlorine and fluorine
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl;
  • R 7 is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxyme- thyl, methoxyethyl and ethoxymethyl;
  • variables R 1 , R 2 , R 3 , R 4 and R 5 together form one of the following substitution patterns on the phenyl ring of compounds of formula I, provided that position 1 is the attachment point of the phenyl ring to the remainder of the molecule:
  • Examples of preferred compounds I.A, where X is N, are the individual compounds compiled in Tables 1 to 15 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment
  • Table 1 Compounds of formula I.A (I.A-1 .1 - I.A-1.2048) in which R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 4 Compounds of formula I.A (I.A-4.1 - I.A-4.2048) in which R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 5 Compounds of formula I .A (I.A-5.1 - I.A-5.2048) in which R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 7 Compounds of formula I .A (I.A-7.1 - I.A-7.2048) in which R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 8 Compounds of formula I .A (I.A-8.1 - I.A-8.2048) in which R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 Compounds of formula I.A (I.A-1 1.1 - I.A-1 1 .2048) in which R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 12 Compounds of formula I.A (I.A-12.1 - I.A-12.2048) in which R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 13 Compounds of formula I.A (I.A-13.1 - I.A-13.2048) in which R 4 is CH 3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 14 Compounds of formula I.A (I.A-14.1 - I.A-14.2048) in which R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 15 Compounds of formula I.A (I.A-15.1 - I.A-15.2048) in which R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A; Table A
  • A-141 1 CH2OCH2CH2OCH3 CN CH 3 CH2CH2CH3
  • Examples of preferred compounds I.B, where X is CR 2 are the individual compounds compiled in Tables 16 to 210 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a par- ticularly preferred embodiment of the substituents in question.
  • Table 17 Compounds of formula I.B1 (I.B1 -2.1 - II.B1 -2.2048) in which R 2 is H, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 18 Compounds of formula I.B1 (I.B1 -3.1 - I.B1 -3.2048) in which R 2 is H, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 20 Compounds of formula I.B1 (I.B1 -5.1 - I.B1 -5.2048) in which R 2 is H, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 22 Compounds of formula I.B1 (I.B1 -7.1 - I.B1 -7.2048) in which R 2 is H, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 23 Compounds of formula I.B1 (I.B1 -8.1 - I.B1 -8.2048) in which R 2 is H, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 24 Compounds of formula I.B1 (I.B1 -9.1 - I.B1 -9.2048) in which R 2 is H, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 25 Compounds of formula I.B1 (I.B1 -10.1 - I.B1 -10.2048) in which R 2 is H, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 26 Compounds of formula I.B1 (I.B1 -1 1 .1 - I.B1 -1 1 .2048) in which R 2 is H, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 27 Compounds of formula I.B1 (I.B1 -12.1 - I.B1 -12.2048) in which R 2 is H, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 28 Compounds of formula I.B1 (I.B1 -13.1 - I.B1 -13.2048) in which R 2 is H, R 4 is CH 3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 29 Compounds of formula I.B1 (I.B1 -14.1 - I.B1 -14.2048) in which R 2 is H, R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 30 Compounds of formula I.B1 (I.B1 -15.1 - I.B1 -15.2048) in which R 2 is H, R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 32 Compounds of formula I.B2 (I.B2-2.1 - ll.B2-2.2048) in which R 2 is methyl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 34 Compounds of formula I.B2 (I.B2-4.1 - I.B2-4.2048) in which R 2 is methyl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 36 Compounds of formula I.B2 (I.B2-6.1 - I.B2-6.2048) in which R 2 is methyl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 37 Compounds of formula I.B2 (I.B2-7.1 - I.B2-7.2048) in which R 2 is methyl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 39 Compounds of formula I.B2 (I.B2-9.1 - I.B2-9.2048) in which R 2 is methyl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 40 Compounds of formula I.B2 (I.B2-10.1 - I.B2-10.2048) in which R 2 is methyl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 42 Compounds of formula I.B2 (I.B2-12.1 - I.B2-12.2048) in which R 2 is methyl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 45 Compounds of formula I.B2 (I.B2-15.1 - I.B2-15.2048) in which R 2 is methyl, R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 46 Compounds of formula I.B3 (I.B3-1 .1 - I.B3-1 .2048) in which R 2 is methylthio, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 47 Compounds of formula I.B3 (I.B3-2.1 - ll.B3-2.2048) in which R 2 is methylthio, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 48 Compounds of formula I.B3 (I.B3-3.1 - I.B3-3.2048) in which R 2 is methylthio, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 49 Compounds of formula I.B3 (I.B3-4.1 - I.B3-4.2048) in which R 2 is methylthio, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 50 Compounds of formula I.B3 (I.B3-5.1 - I.B3-5.2048) in which R 2 is methylthio, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 52 Compounds of formula I.B3 (I.B3-7.1 - I.B3-7.2048) in which R 2 is methylthio, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 54 Compounds of formula I.B3 (I.B3-9.1 - I.B3-9.2048) in which R 2 is methylthio, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 55 Compounds of formula I.B3 (I.B3-10.1 - I.B3-10.2048) in which R 2 is methylthio, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 56 Compounds of formula I.B3 (I.B3-1 1 .1 - I.B3-1 1 .2048) in which R 2 is methylthio, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 57 Compounds of formula I.B3 (I.B3-12.1 - I.B3-12.2048) in which R 2 is methylthio, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 58 Compounds of formula I.B3 (I.B3-13.1 - I.B3-13.2048) in which R 2 is methylthio, R 4 is CH 3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 60 Compounds of formula I.B3 (I.B3-15.1 - I.B3-15.2048) in which R 2 is methylthio, R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 61 Compounds of formula I.B4 (I.B4-1 .1 - I.B4-1 .2048) in which R 2 is ethylthio, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 62 Compounds of formula I.B4 (I.B4-2.1 - ll.B4-2.2048) in which R 2 is ethylthio, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 63 Compounds of formula I.B4 (I.B4-3.1 - I.B4-3.2048) in which R 2 is ethylthio, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 64 Compounds of formula I.B4 (I.B4-4.1 - I.B4-4.2048) in which R 2 is ethylthio, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 65 Compounds of formula I.B4 (I.B4-5.1 - I.B4-5.2048) in which R 2 is ethylthio, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 66 Compounds of formula I.B4 (I.B4-6.1 - I.B4-6.2048) in which R 2 is ethylthio, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 68 Compounds of formula I.B4 (I.B4-8.1 - I.B4-8.2048) in which R 2 is ethylthio, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 69 Compounds of formula I.B4 (I.B4-9.1 - I.B4-9.2048) in which R 2 is ethylthio, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 70 Compounds of formula I.B4 (I.B4-10.1 - I.B4-10.2048) in which R 2 is ethylthio, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 72 Compounds of formula I.B4 (I.B4-12.1 - I.B4-12.2048) in which R 2 is ethylthio, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 74 Compounds of formula I.B4 (I.B4-14.1 - I.B4-14.2048) in which R 2 is ethylthio, R 4 is CH 3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 75 Compounds of formula I.B4 (I.B4-15.1 - I.B4-15.2048) in which R 2 is ethylthio, R 4 is CH 3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 76 Compounds of formula I.B5 (I.B5-1 .1 - I.B5-1 .2048) in which R 2 is methylsulfonyl, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 77 Compounds of formula I.B5 (I.B5-2.1 - ll.B5-2.2048) in which R 2 is methylsulfonyl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 78 Compounds of formula I.B5 (I.B5-3.1 - I.B5-3.2048) in which R 2 is methylsulfonyl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 79 Compounds of formula I.B5 (I.B5-4.1 - I.B5-4.2048) in which R 2 is methylsulfonyl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 80 Compounds of formula I.B5 (I.B5-5.1 - I.B5-5.2048) in which R 2 is methylsulfonyl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 81 Compounds of formula I.B5 (I.B5-6.1 - I.B5-6.2048) in which R 2 is methylsulfonyl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 82 Compounds of formula I.B5 (I.B5-7.1 - I.B5-7.2048) in which R 2 is methylsulfonyl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 83 Compounds of formula I.B5 (I.B5-8.1 - I.B5-8.2048) in which R 2 is methylsulfonyl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 84 Compounds of formula I.B5 (I.B5-9.1 - I.B5-9.2048) in which R 2 is methylsulfonyl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 85 Compounds of formula I.B5 (I.B5-10.1 - I.B5-10.2048) in which R 2 is methylsulfonyl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 86 Compounds of formula I.B5 (I.B5-1 1 .1 - I.B5-1 1 .2048) in which R 2 is methylsulfonyl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 87 Compounds of formula I.B5 (I.B5-12.1 - I.B5-12.2048) in which R 2 is methylsulfonyl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 88 Compounds of formula I.B5 (I.B5-13.1 - I.B5-13.2048) in which R 2 is methylsulfonyl, R 4 is CH 3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 89 Compounds of formula I.B5 (I.B5-14.1 - I.B5-14.2048) in which R 2 is methylsulfonyl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 90 Compounds of formula I.B5 (I.B5-15.1 - I.B5-15.2048) in which R 2 is methylsulfonyl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 92 Compounds of formula I.B6 (I.B6-2.1 - ll.B6-2.2048) in which R 2 is ethylsulfonyl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 93 Compounds of formula I.B6 (I.B6-3.1 - I.B6-3.2048) in which R 2 is ethylsulfonyl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 94 Compounds of formula I.B6 (I.B6-4.1 - I.B6-4.2048) in which R 2 is ethylsulfonyl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 95 Compounds of formula I.B6 (I.B6-5.1 - I.B6-5.2048) in which R 2 is ethylsulfonyl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 96Compounds of formula I.B6 (I.B6-6.1 - I.B6-6.2048) in which R 2 is ethylsulfonyl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 97 Compounds of formula I.B6 (I.B6-7.1 - I.B6-7.2048) in which R 2 is ethylsulfonyl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 101 Compounds of formula I.B6 (I.B6-1 1 .1 - I.B6-1 1 .2048) in which R 2 is ethylsulfonyl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 102 Compounds of formula I.B6 (I.B6-12.1 - I.B6-12.2048) in which R 2 is ethylsulfonyl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 103 Compounds of formula I.B6 (I.B6-13.1 - I.B6-13.2048) in which R 2 is ethylsulfonyl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 104 Compounds of formula I.B6 (I.B6-14.1 - I.B6-14.2048) in which R 2 is ethylsulfonyl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 105 Compounds of formula I.B6 (I.B6-15.1 - I.B6-15.2048) in which R 2 is ethylsulfonyl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 106 Compounds of formula I.B7 (I.B7-1 .1 - I.B7-1 .2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 107 Compounds of formula I.B7 (I.B7-2.1 - ll.B7-2.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 108 Compounds of formula I.B7 (I.B7-3.1 - I.B7-3.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 109 Compounds of formula I.B7 (I.B7-4.1 - I.B7-4.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 1 1 Compounds of formula I.B7 (I.B7-6.1 - I.B7-6.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 13Compounds of formula I.B7 (I.B7-8.1 - I.B7-8.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 14 Compounds of formula I.B7 (I.B7-9.1 - I.B7-9.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 15 Compounds of formula I.B7 (I.B7-10.1 - I.B7-10.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 16Compounds of formula I.B7 (I.B7-1 1 .1 - I.B7-1 1 .2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 17 Compounds of formula I.B7 (I.B7-12.1 - I.B7-12.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 18Compounds of formula I.B7 (I.B7-13.1 - I.B7-13.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 1 19Compounds of formula I.B7 (I.B7-14.1 - I.B7-14.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 120 Compounds of formula I.B7 (I.B7-15.1 - I.B7-15.2048) in which R 2 is trifluoromethyl- methoxymethyl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 121 Compounds of formula I.B8 (I.B8-1 .1 - I.B8-1 .2048) in which R 2 is isoxazolin-3-yl, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 122Compounds of formula I.B8 (I.B8-2.1 - ll.B8-2.2048) in which R 2 is isoxazolin-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 124 Compounds of formula I.B8 (I.B8-4.1 - I.B8-4.2048) in which R 2 is isoxazolin-3-yl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 125 Compounds of formula I.B8 (I.B8-5.1 - I.B8-5.2048) in which R 2 is isoxazolin-3-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 126Compounds of formula I.B8 (I.B8-6.1 - I.B8-6.2048) in which R 2 is isoxazolin-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 127Compounds of formula I.B8 (I.B8-7.1 - I.B8-7.2048) in which R 2 is isoxazolin-3-yl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 128Compounds of formula I.B8 (I.B8-8.1 - I.B8-8.2048) in which R 2 is isoxazolin-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 129Compounds of formula I.B8 (I.B8-9.1 - I.B8-9.2048) in which R 2 is isoxazolin-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 130 Compounds of formula I.B8 (I.B8-10.1 - I.B8-10.2048) in which R 2 is isoxazolin-3-yl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 131 Compounds of formula I.B8 (I.B8-1 1 .1 - I.B8-1 1 .2048) in which R 2 is isoxazolin-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 132Compounds of formula I.B8 (I.B8-12.1 - I.B8-12.2048) in which R 2 is isoxazolin-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 133Compounds of formula I.B8 (I.B8-13.1 - I.B8-13.2048) in which R 2 is isoxazolin-3-yl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 134Compounds of formula I.B8 (I.B8-14.1 - I.B8-14.2048) in which R 2 is isoxazolin-3-yl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 135 Compounds of formula I.B8 (I.B8-15.1 - I.B8-15.2048) in which R 2 is isoxazolin-3-yl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 136 Compounds of formula I.B9 (I.B9-1 .1 - I.B9-1 .2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 137 Compounds of formula I.B9 (I.B9-2.1 - ll.B9-2.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 138 Compounds of formula I.B9 (I.B9-3.1 - I.B9-3.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 139 Compounds of formula I.B9 (I.B9-4.1 - I.B9-4.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 140 Compounds of formula I.B9 (I.B9-5.1 - I.B9-5.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 141 Compounds of formula I.B9 (I.B9-6.1 - I.B9-6.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 142 Compounds of formula I.B9 (I.B9-7.1 - I.B9-7.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 143 Compounds of formula I.B9 (I.B9-8.1 - I.B9-8.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 144Compounds of formula I.B9 (I.B9-9.1 - I.B9-9.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 145 Compounds of formula I.B9 (I.B9-10.1 - I.B9-10.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 146 Compounds of formula I.B9 (I.B9-1 1 .1 - I.B9-1 1 .2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 147 Compounds of formula I.B9 (I.B9-12.1 - I.B9-12.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 148 Compounds of formula I.B9 (I.B9-13.1 - I.B9-13.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 149 Compounds of formula I.B9 (I.B9-14.1 - I.B9-14.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 150 Compounds of formula I.B9 (I.B9-15.1 - I.B9-15.2048) in which R 2 is 5-methyl- isoxazolin-3-yl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 151 Compounds of formula I.B10 (I.B10-1 .1 - I.B10-1.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 152 Compounds of formula I.B10 (I.B10-2.1 - II. B10-2.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 153 Compounds of formula I.B10 (I.B10-3.1 - I.B10-3.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 154 Compounds of formula I.B10 (I.B10-4.1 - I.B10-4.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 155 Compounds of formula I.B10 (I.B10-5.1 - I.B10-5.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 156 Compounds of formula I.B10 (I.B10-6.1 - I.B10-6.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 157Compounds of formula I.B10 (I.B10-7.1 - I.B10-7.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 158 Compounds of formula I.B10 (I.B10-8.1 - I.B10-8.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 159 Compounds of formula I.B10 (I.B10-9.1 - I.B10-9.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 160Compounds of formula I.B10 (I.B10-10.1 - I.B10-10.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 161 Compounds of formula I.B10 (I.B10-1 1 .1 - I.B10-1 1 .2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 162 Compounds of formula I.B10 (I.B10-12.1 - I.B10-12.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 163 Compounds of formula I.B10 (I.B10-13.1 - I.B10-13.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 164 Compounds of formula I.B10 (I.B10-14.1 - I.B10-14.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 165 Compounds of formula I.B10 (I.B10-15.1 - I.B10-15.2048) in which R 2 is 3-methyl- isoxazolin-5-yl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 166Compounds of formula I.B1 1 (I.B1 1 -1 .1 - I.B1 1 -1.2048) in which R 2 is isoxazol-3-yl, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 167Compounds of formula I.B1 1 (I. B1 1 -2.1 - II. B1 1 -2.2048) in which R 2 is isoxazol-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 168Compounds of formula I.B1 1 (I. B1 1 -3.1 - 1. B1 1 -3.2048) in which R 2 is isoxazol-3-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 170 Compounds of formula I.B1 1 (I. B1 1 -5.1 - 1. B1 1 -5.2048) in which R 2 is isoxazol-3-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 171 Compounds of formula I.B1 1 (I. B1 1 -6.1 - 1. B1 1 -6.2048) in which R 2 is isoxazol-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 172 Compounds of formula I.B1 1 (I. B1 1 -7.1 - 1. B1 1 -7.2048) in which R 2 is isoxazol-3-yl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 173 Compounds of formula I.B1 1 (I. B1 1 -8.1 - 1. B1 1 -8.2048) in which R 2 is isoxazol-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 174 Compounds of formula I.B1 1 (I. B1 1 -9.1 - 1. B1 1 -9.2048) in which R 2 is isoxazol-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 175 Compounds of formula I.B1 1 (I. B1 1 -10.1 - 1. B1 1 -10.2048) in which R 2 is isoxazol-3-yl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 176 Compounds of formula I.B1 1 (I. B1 1 -1 1 .1 - I.B1 1 -1 1 .2048) in which R 2 is isoxazol-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 177 Compounds of formula I.B1 1 (I. B1 1 -12.1 - 1. B1 1 -12.2048) in which R 2 is isoxazol-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 178 Compounds of formula I.B1 1 (I. B1 1 -13.1 - 1. B1 1 -13.2048) in which R 2 is isoxazol-3-yl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 179 Compounds of formula I.B1 1 (I. B1 1 -14.1 - 1. B1 1 -14.2048) in which R 2 is isoxazol-3-yl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A; Table 180Compounds of formula I.B1 1 (I. B1 1 -15.1 - 1.
  • Table 182 Compounds of formula I.B12 (I.B12-2.1 - ll.B12-2.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound cor- responds in each case to one row of Table A;
  • Table 184 Compounds of formula I.B12 (I.B12-4.1 - I.B12-4.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is F and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 185 Compounds of formula I.B12 (I.B12-5.1 - I.B12-5.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 186 Compounds of formula I.B12 (I.B12-6.1 - I.B12-6.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 187 Compounds of formula I.B12 (I.B12-7.1 - I.B12-7.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound cor- responds in each case to one row of Table A;
  • Table 188 Compounds of formula I.B12 (I.B12-8.1 - I.B12-8.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 189 Compounds of formula I.B12 (I.B12-9.1 - I.B12-9.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 190Compounds of formula I.B12 (I.B12-10.1 - I.B12-10.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 191 Compounds of formula I.B12 (I.B12-1 1 .1 - I.B12-1 1 .2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 192 Compounds of formula I.B12 (I.B12-12.1 - I.B12-12.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 193 Compounds of formula I.B12 (I.B12-13.1 - I.B12-13.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 194 Compounds of formula I.B12 (I.B12-14.1 - I.B12-14.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 195 Compounds of formula I.B12 (I.B12-15.1 - I.B12-15.2048) in which R 2 is 5-methyl- isoxazol-3-yl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 196 Compounds of formula I.B13 (I.B13-1 .1 - I.B13-1.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is H and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 197 Compounds of formula I.B13 (I.B13-2.1 - II. B13-2.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is H and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 198 Compounds of formula I.B13 (I.B13-3.1 - I.B13-3.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is H and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 200 Compounds of formula I.B13 (I.B13-5.1 - I.B13-5.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is F and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound cor- responds in each case to one row of Table A;
  • Table 201 Compounds of formula I.B13 (I.B13-6.1 - I.B13-6.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is F and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 202 Compounds of formula I.B13 (I.B13-7.1 - I.B13-7.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CI and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 203 Compounds of formula I.B13 (I.B13-8.1 - I.B13-8.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CI and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 204 Compounds of formula I.B13 (I.B13-9.1 - I.B13-9.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CI and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 205 Compounds of formula I.B13 (I.B13-10.1 - I.B13-10.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CN and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 206 Compounds of formula I.B13 (I.B13-1 1 .1 - I.B13-1 1 .2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CN and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 207 Compounds of formula I.B13 (I.B13-12.1 - I.B13-12.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CN and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 208Compounds of formula I.B13 (I.B13-13.1 - I.B13-13.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CH3 and R 5 is H and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 209 Compounds of formula I.B13 (I.B13-14.1 - I.B13-14.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CH3 and R 5 is F and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • Table 210 Compounds of formula I.B13 (I.B13-15.1 - I.B13-15.2048) in which R 2 is 3-methyl- isoxazol-5-yl, R 4 is CH3 and R 5 is CI and the combination of R 1 , R 3 , R 6 and R 7 for a compound corresponds in each case to one row of Table A;
  • the compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described hereinafter in schemes 1 to 4.
  • the substituents, variables and indices in schemes 1 to 4 are as defined above for formula I, if not otherwise specified.
  • N-R 6 -4-R 7 -1 ,2,4-triazol-3-amine compounds of formula III can be reacted with benzoyl derivatives of formula II to afford compounds of formula I.
  • X is a leaving group, such as halogen, in particular CI, an anhydride residue or an activated ester or activated amide residue.
  • a base is for example carbonates, such as lithium, sodium or potassium carbonates, amines, such as trimethylamine or triethylamine, and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or 2,4,6-trimethylpyridine.
  • Suitable solvents are in particular aprotic sol- vents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1 ,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trime- thylbenzene, pyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1 ,4-dioxane, N,N-dimethyl formamide, N-methyl pyrrolidinone or mixtures thereof.
  • the starting materials are generally re- acted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of
  • compounds of formula I can also be prepared as shown in Scheme 2.
  • Reaction of N-R 6 -4-R 7 -1 ,2,4-triazol-3-amine of formula III with a benzoic acid derivative of formula IV yields compound I.
  • the reaction is preferably carried out in the presence of a suitable activating agent, which converts the carboxylic acid group of compound IV into an activated ester or an activated amide of formula II.
  • activating agents known in the art such as 1 ,1 ',carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1 -ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC), 2,4,6-tripropyl-1 ,3,5,2,4,6-trioxatriphosphorinane- 2,4,6-trioxide (T3P) or 1 -propanephosphonic acid cyclic anhydride (PPAA) can be employed.
  • CDI 1,1 ',carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • EDC 1 -ethyl-3-(3- dimethylaminopropyl)carbodiimide
  • T3P 2,4,6-tripropyl-1 ,3,5,2,4,6-trioxatriphosphorinane- 2,4,6-trioxide
  • PPAA 1 -propane
  • the activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting compound IV with the activating agent in the presence of compound III, or in a separate step prior to the reaction with compound III. It may be advantageous, especially in cases where DCC, EDC and PPAA are used as activating agent, to include further additives in the activating reaction, such as hydroxybenzotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4,5-trichlorophenol, N-hydroxysuccinimide or 4-Dimethylamino-pyridine (DMAP). It may further be advantageous to prepare the activated ester or amide in the presence of a base, for example a tertiary amine.
  • a base for example a tertiary amine.
  • the activated ester or amide is either in situ or subsequently reacted with the amine of formula III to afford the amide of formula I.
  • the reaction normally takes place in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. di- chloromethane or dichloroethane, ethers, e.g. tetrahydrofuran or 1 ,4-dioxane or carboxamides, e.g. N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide or N-methylpyrrolidone.
  • the reaction is ordinarily carried out at temperatures in the range from -20°C to +25°C.
  • the compounds of formula II and their respective benzoic acid precursors of formula IV can be purchased or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO 9746530, WO 9831676, WO 9831681 , WO 2002/018352, WO 2000/003988, US
  • compounds of formula I, where R 6 is not hydrogen can be obtained by treating N-(4-R 7 -1 ,2,4-triazol-3-yl)benzamides of formula V with, for example, alkylating agents such as alkyl halides according to Scheme 3.
  • the 4-R ,2,4-triazol-3-amine of formula III, where R 7 is for example alkyl, can be prepared in a two steps manner (scheme 4).
  • the first step consists of alkylating commercially available 5- nitro-1 H-1 ,2,4-Triazole with an alkylating agent such as a alkyl halide or a dialkylsuflate.
  • an alkylating agent such as a alkyl halide or a dialkylsuflate.
  • the second step is the reduction of the nitro group to the amino group. This reaction is done by known catalytic hydrogenation methods (Pd, Pt, Ni and Zn) or by Metal (Iron, Tin) reduction in acetic medium such as acetic acid or HCI.
  • the compounds of formula I including their stereoisomers, salts, tautomers and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds of formula I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
  • reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystalliza- tion or trituration.
  • the compounds of formula I and their agriculturally suitable salts are useful as herbicides. They are useful as such or as an appropriately formulated composition.
  • the herbicidal compositions comprising the compound I in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • the compounds of formula I, in particu- lar the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted plants.
  • suitable crops are the following:
  • crop plants also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information).
  • genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information).
  • one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.
  • crop plants also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, US 5,013,659) or imidazolinones (see, for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as, for example, glypho- sate (see, for example, WO WO glypho-
  • Crop plants for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (muta- genesis).
  • Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady ® (glypho- sate) and Liberty Link ® (glufosinate) have been generated with the aid of genetic engineering methods.
  • crop plants also includes plants which, with the aid of genetic en- gineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp.
  • Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B.
  • VI Ps vegetative insecticidal proteins
  • VI Ps vegetative insecticidal proteins
  • toxins of animal organisms for example wasp, spider or scorpion toxins
  • fungal toxins for example from Strep- tomycetes
  • plant lectins for example from peas or barley
  • agglutinins proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribo- some-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin
  • steroid-metabolizing enzymes for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase
  • ion channel blockers for example inhibitors of sodium channels or calcium channels
  • juvenile hormone esterase for example from Bacillus subtilis, Xenorhabdus spp.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1 ), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1 F and the PAT enzyme).
  • crop plants also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • resistance proteins for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum
  • T4 lysozyme for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora.
  • crop plants also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
  • potential yield for example biomass, grain yield, starch, oil or protein content
  • tolerance to drought for example drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
  • crop plants also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for ex- ample by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsatu- rated omega 9 fatty acids (for example Nexera ® oilseed rape).
  • crop plants also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora ® potato).
  • the compounds of formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • compositions for the desiccation and/or defoliation of plants processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.
  • the compounds of formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • the compounds of formula I, or the herbicidal compositions comprising the compounds of formula I can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed.
  • the use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.
  • the herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.
  • auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.
  • surfactants such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers
  • organic and inorganic thickeners such as bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.
  • thickeners i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion
  • polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).
  • antifoams examples include silicone emulsions (such as, for example, Silikon ® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides can be added for stabilizing the aqueous herbicidal formulation.
  • bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both sparingly water-soluble pigments and water-soluble dyes.
  • Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1 , and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • Suitable inert auxiliaries are, for example, the following:
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
  • paraffin tetrahydronaphthalene
  • alkylated naphthalenes and their derivatives alkylated benzenes and their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclohexanone or strongly polar
  • Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea
  • Suitable surfactants adjuvants, wetting agents, tackifiers, dispersants and also
  • emulsifiers are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard),
  • dibutylnaphthalenesulfonic acid Nakal types, BASF SE
  • fatty acids alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, iso
  • methylcellulose methylcellulose
  • hydrophobically modified starches polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the compounds of formula I or la, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
  • concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
  • concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges.
  • the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound.
  • the active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.
  • the compounds of formula I of the invention can for example be formulated as follows: 1 . Products for dilution with water
  • active compound 10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.
  • active compound 20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexa- none with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.
  • a dispersant for example polyvinylpyrrolidone.
  • the active compound content is 20% by weight.
  • active compound 15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion.
  • the formulation has an active compound content of 15% by weight.

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Abstract

N-(1,2,4-triazol-3-yl)arylcarboxamides of formula (I) and their use as herbicides. The invention relates to N-(1,2,4-triazol-3-yl)arylcarboxamides of formula (I) and their use as herbicides. In said formula (I), X represents N or CR2, whereas R1, R2, R3, R4, R5, R6 and R7 represent groups such as hydrogen, halogen or organic groups such as alkyl or phenyl.

Description

Substituted N-(1 ,2,4-triazol-3-yl)arylcarboxamide compounds and their use as herbicides
Description The present invention relates to substituted N-(1 ,2,4-triazol-3-yl)arylcarboxamide compounds and the N-oxides and salts thereof and to compositions comprising the same. The invention also relates to the use of the N-(1 ,2,4-triazol-3-yl)arylcarboxamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation.
Furthermore, the invention relates to methods of applying such compounds.
For the purposes of controlling unwanted vegetation, especially in crops, there is an ongoing need for new herbicides which have high activities and selectivities together with a substantial lack of toxicity for humans and animals.
WO 2012/028579 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 3- and 4-positions of the aryl ring and their use as herbi- cides.
WO2013/087577 describes certain N-(tetrazol-4-yl) and N-(triazol-3-yl)arylcarboxylic acid amides, which additionally carry a substituent on the benzamide nitrogen and their use as herbicides.
WO2013/144234 also discloses 1 ,2,4-triazole derivatives as herbicides.
The compounds of the prior art often suffer form insufficient herbicidal activity in particular at low application rates and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.
Accordingly, it is an object of the present invention to provide further N-(1 ,2,4-triazol-3- yl)arylcarboxamide compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and/or a high compatibility with crop plants. The N-(1 ,2,4-triazol-3-yl)arylcarboxamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.
These and further objectives are achieved by the compounds of formula I defined below and their N-oxides and also their agriculturally suitable salts.
It has been found that the above objectives can be achieved by substituted N-(1 ,2,4- triazol-3-yl)arylcarboxamide compounds of the general formula I, as defined below, including their N-oxides and their salts, in particular their agriculturally suitable salts.
Therefore, in a first as relates to compounds of formula I,
Figure imgf000002_0001
wherein R1 is selected from the group consisting of cyano-Z1, halogen, nitro, d-Cs-alkyl, C2-C8- alkenyl, C2-C8-alkynyl, C3-Cio-cycloalkyl-Z1, C-i-Cs-haloalkyl, C2-C8-haloalkenyl, C3- Cs-haloalkynyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Z1, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1, and heterocyclyloxy-Z1, where heterocy- clyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubsti- tuted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different;
X is N or CR2;
R2, R3 are identical or different and independently selected from the group consisting of hydrogen, halogen, OH-Z2, NO2-Z2, cyano-Z2, Ci-C6-alkyl, C2-Cs-alkenyl, C2-C8- alkynyl, C3-Cio-cycloalkyl-Z2, C3-Cio-cycloalkoxy-Z2, where the C3-Cio-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, Cs-Cs-haloalkynyl, d-Cs-alkoxy- Z2, Ci-Cs-haloalkoxy-Z2, C3-Cio-cycloalkyl- Ci-C2-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy- Z2, Ci-C4-alkylthio-Ci-C4-alkylthio-Z2, C2-C8-alkenyloxy-Z2, C2-C8-alkynyloxy-Z2, C2- Cs-haloalkenyloxy-Z2, Cs-Cs-haloalkynyloxy-Z2, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z2, (tri-Ci-C4-alkyl)silyl-Z2, R2b-S(0)k-Z2, R2c-C(=0)-Z2, R2dO-C(=0)-Z2, R2dO-N=CH-Z2,
Figure imgf000003_0001
R2eR2f N-C(=0)-Z2, R¾R2hN-Z2, phenyl-Z2a and heterocy- clyl-Z2a, where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10- membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z2a and heterocy- clyl-Z2a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R21 , which are identical or different; or
R2 and R3 together form a saturated 5- or 6-membered ring, optionally containing an oxygen or a S(0)n heteroatom, the 5- or 6-membered ring being unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy;
R4 is selected from the group consisting of hydrogen, cyano- Z1 , halogen, nitro, Ci-Cs- alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci- C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phe- noxy-Z1 and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different;
R5 is selected from the group consisting of cyano- Z1, halogen, nitro, Ci-Cs-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino,
Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4- alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1 and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different;
R6 is selected from the group consisting of hydrogen, CN, nitro, hydroxy, amino, C1-C6- alkyl, Ci-C6-cya no-alky I, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or par- tially or completely halogenated, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylcarbonyl,
Ci-C6-alkyaminocarbonyl, Ci-C6-dialkyl-aminocarbonyl, Ci-C6-alkyamino, C1-C6- dialkyl-amino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, RbRbN-S(0)n-Z, R O-S(0)n- Z, R -S(0)n-Z, RcRcN-Ci-C3-alkyl-S(0)n-Ci-C3-alkyl,
Figure imgf000004_0001
Rd- C(=0)0-Ci-C3-alkyl , Rd-0-C(=0)0-Ci-C3-alkyl ,RdO-C(=0)-Ci-C3-alkyl, ReRfN-
C(=0)-Ci-C3-alkyl,
Figure imgf000004_0002
R -S(0)n-ReN-Ci-C3-alkyl, RCRCN-Ci- C3-alkyl, phenyl-Z and heterocyclyl-Z, where heterocyclyl is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups R', which are identical or different;
R7 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy, Ci- C4-alkoxy-Ci-C4-alkyl and Ci-C4-haloalkoxy-Ci-C4-alkyl; n is 0, 1 or 2; k is 0, 1 or 2;
R', R11, R21 independently of each other are selected from the group consisting of
halogen, N02, CN, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, Ci-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, d-Ce-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C3-C7-cycloalkoxy and Ci- C6-haloalkyloxy, or two vicinal radicals R', R11 or R21 together may form a group =0;
Z, Z1, Z2 independently of each other are selected from the group consisting of a
covalent bond and Ci-C4-alkanediyl; Z2a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-
Ci-C4-alkanediyl, Ci-C4-alkanediyl-0 and
Ci-C4-alkanediyl-0-Ci-C4-alkanediyl;
Rb, R1b, R2b independently of each other are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-
C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
Rc, R2c independently of each other are selected from the group consisting of
hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
Rd, R2d independently of each other are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; Re, Rf independently of each other are selected from the group consisting of
hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, or
Re, Rf together with the nitrogen atom, to which they are bound may form a 5-, 6 or
7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R2e, R2f independently of each other have the meanings given for Re, Rf;
R9 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, C1-C4- alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-
C4-alkoxy and Ci-C4-haloalkoxy;
Rh is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, C1-C4- alkylcarbonyl, a radical C(=0)-Rk, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or
R9, Rh together with the nitrogen atom, to which they are bound may form a 5-, 6 or
7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R¾, R2h independently of each other have the meanings given for Rs, Rh;
Rk has the meanings given for Rc; an N-oxide or an agriculturally suitable salt thereof.
The compounds of the present invention, i.e. the compounds of formula I, their N-oxides, or their salts are particularly useful for controlling unwanted vegetation. Therefore, the invention also relates to the use of a compound of the present invention, an N-oxide or a salt thereof or of a composition comprising at least one compound of the invention, an N-oxide or an agricultural- ly suitable salt thereof for combating or controlling unwanted vegetation.
The invention also relates to a composition comprising at least one compound according to the invention, including an N-oxide or a salt thereof, and at least one auxiliary. In particular, the invention relates to an agricultural composition comprising at least one compound according to the invention including an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary customary for crop protection formulations.
The present invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound according to the invention, including an N-oxide or a salt thereof, to act on unwanted plants, their seed and/or their habitat.
Depending on the substitution pattern, the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
Depending on the substitution pattern, the compounds of formula I may be present in the form of their tautomers. Hence the invention also relates to the tautomers of the formula I and the stereoisomers, salts and N-oxides of said tautomers.
The term "N-oxide" includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides in compounds of formula I can in particular be prepared by oxidizing the ring nitrogen atom(s) of the N-(1 ,2,4-triazol- 3-yl)arylcarboxamide ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides, or the ring nitrogen atom(s) of a heterocyclic substituent R, R1, R2 or R3.
The present invention moreover relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably nonradioactive isotope (e.g., hydrogen by deuterium, 12C by 13C, 14N by 15N, 160 by 180) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom. Of course, the compounds according to the invention contain more of the respective isotope than this naturally occurs and thus is anyway present in the compounds of formula I.
The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of formula I, their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
Useful agriculturally suitable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, C1-C4- hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isoprop- ylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetrame- thylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensul- fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The term "undesired vegetation" ("weeds") is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location.
The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn- Cm indicates in each case the possible number of carbon atoms in the group.
The term "halogen" denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
The term "partially or completely halogenated" will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. A partially or completely halogenated radical is termed below also "halo-radical". For example, partially or completely halogenated alkyl is also termed haloalkyl.
The term "alkyl" as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 car- bon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms. Examples of Ci-C4-alkyl are methyl, ethyl, n-propyl, iso-propyl, n- butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl. Examples for Ci-C6-alkyl are, apart those mentioned for Ci-C4-alkyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methylpropyl. Examples for Ci-Cio-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2- methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1 -ethylpentyl, 2-ethylpentyl, 3- ethylpentyl, n-octyl, 1 -methyloctyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propylpentyl, 2-propylpentyl, nonyl, decyl, 2-propylheptyl and 3-propylheptyl.
The term "alkylene" (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
The term "haloalkyl" as used herein (and in the haloalkyl moieties of other groups com- prising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms ("Ci-Cs-haloalkyl"), frequently from 1 to 6 carbon atoms ("C1-C6- haloalkyl"), more frequently 1 to 4 carbon atoms ("Ci-C4-haloalkyl"), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moie- ties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halomethyl, in particular from Ci-C2-fluoroalkyl. Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like. Examples for Ci-C2-fluoroalkyl are fluo- romethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, pentafluoroethyl, and the like. Examples for Ci-C2-haloalkyl are, apart those mentioned for Ci-C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 2-chloroethyl, 2,2,- dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 1 -bromoethyl, and the like. Examples for Ci-C4-haloalkyl are, apart those mentioned for Ci-C2-haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trif I uoroprop-2-yl , 3-chloropropyl, 4-chlorobutyl and the like.
The term "cycloalkyi" as used herein (and in the cycloalkyi moieties of other groups com- prising a cycloalkyi group, e.g. cycloalkoxy and cycloalkylalkyi) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms ("C3-Cio-cycloalkyl"), preferably 3 to 7 carbon atoms ("C3-C7-cycloalkyl") or in particular 3 to 6 carbon atoms ("C3-C6- cycloalkyl"). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
The term "halocycloalkyl" as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are
1 - and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1 -,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.
The term "cycloalkyl-alkyl" used herein denotes a cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkylene group. The term "C3-C7- cycloalkyl-Ci-C4-alkyl" refers to a C3-C7-cycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above. Examples are cyclo- propylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobu- tylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclo- hexylethyl, cyclohexylpropyl, and the like.
The term "alkenyl" as used herein denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 ("C2-C8-alkenyl"), preferably 2 to 6 carbon atoms ("C2-C6-alkenyl"), in particular 2 to 4 carbon atoms ("C2-C4-alkenyl"), and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 - methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 - methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 - propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1 -butenyl, 1 -methyl-2-butenyl,
2- methyl-2-butenyl, 3-methyl-2-butenyl, 1 -methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3- butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl-1 -propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 - propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl-1 - pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1 -pentenyl, 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl,
2- methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-
3- pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2-butenyl, 1 -ethyl-3-butenyl, 2-ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2- ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 - propenyl, 1 -ethyl-2-methyl-2-propenyl and the like, or C2-Cs-alkenyl, such as the radicals mentioned for C2-C6-alkenyl and additionally 1 -heptenyl, 2-heptenyl, 3-heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl, 4-octenyl and the positional isomers thereof.
The term "haloalkenyl" as used herein, which may also be expressed as "alkenyl which is substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 ("C2-C8-haloalkenyl") or 2 to 6 ("C2-C6-haloalkenyl") or 2 to 4 ("C2-C4-haloalkenyl") carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
The term "alkynyl" as used herein denotes unsaturated straight-chain or branched hydro- carbon radicals having usually 2 to 8 ("C2-C8-alkynyl"), frequently 2 to 6 ("C2-C6-alkynyl"), preferably 2 to 4 carbon atoms ("C2-C4-alkynyl") and a triple bond in any position, for example C2- C4-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 - methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1 ,1 -dimethyl-2- propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2- pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3- methyl-1 -pentynyl, 3-methyl-4-pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1 ,1 -dimethyl- 2-butynyl, 1 ,1 -dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1 - butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl, 1 -ethyl-1 -methyl-2-propynyl and the like.
The term "haloalkynyl" as used herein, which is also expressed as "alkynyl which is substituted by halogen", refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 carbon atoms ("C2-C8-haloalkynyl"), frequently 2 to 6 ("C2-C6-haloalkynyl"), preferabyl 2 to 4 carbon atoms ("C2-C4-haloalkynyl"), and a triple bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms ("d-Cs-alkoxy"), frequently from 1 to 6 carbon atoms ("Ci-C6-alkoxy"), preferably 1 to 4 carbon atoms ("Ci-C4-alkoxy"), which is bound to the remainder of the molecule via an oxygen atom. Ci-C2-Alkoxy is methoxy or ethoxy. C1-C4- Alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy,
1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy). Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2-methylpropoxy. Ci-Cs-Alkoxy is addition- ally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms ("Ci-Cs-haloalkoxy"), frequently from 1 to 6 carbon atoms ("Ci-C6-haloalkoxy"), preferably 1 to 4 carbon atoms ("C1-C4- haloalkoxy"), more preferably 1 to 3 carbon atoms ("Ci-C3-haloalkoxy"), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. Ci-C2-Haloalkoxy is, for example, OCH2F, OCH F2, OCF3, OCH2CI, OCHC , OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5. Ci-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH2F)-2-fluoroethoxy, 1 -(CH2CI)-2-chloroethoxy, 1 -(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
The term "alkoxyalkyl" as used herein denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. "Ci-C6-alkoxy-Ci-C6-alkyl" is a Ci-C6-alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are CH2OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (l -methylpropoxy)-methyl, (2- methylpropoxy)methyl, CH2-OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2- (1 -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1 - methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1 -methylpropoxy)-propyl, 2-(2-methylpropoxy)- propyl, 2-(1 ,1 -dimethylethoxy)-propyl, 3-(methoxy)-propyl, 3-(ethoxy)-propyl, 3-(n-propoxy)- propyl, 3-(1 -methylethoxy)-propyl, 3-(n-butoxy)-propyl, 3-(1 -methylpropoxy)-propyl, 3-(2- methylpropoxy)-propyl, 3-(1 ,1 -dimethylethoxy)-propyl, 2-(methoxy)-butyl, 2-(ethoxy)-butyl, 2-(n- propoxy)-butyl, 2-(1 -methylethoxy)-butyl, 2-(n-butoxy)-butyl, 2-(1 -methylpropoxy)-butyl, 2-(2- methyl-propoxy)-butyl, 2-(1 ,1 -dimethylethoxy)-butyl, 3-(methoxy)-butyl, 3-(ethoxy)-butyl, 3-(n- propoxy)-butyl, 3-(1 -methylethoxy)-butyl, 3-(n-butoxy)-butyl, 3-(1 -methylpropoxy)-butyl, 3-(2- methylpropoxy)-butyl, 3-(1 ,1 -dimethylethoxy)-butyl, 4-(methoxy)-butyl, 4-(ethoxy)-butyl, 4-(n- propoxy)-butyl, 4-(1 -methylethoxy)-butyl, 4-(n-butoxy)-butyl, 4-(1 -methylpropoxy)-butyl, 4-(2- methylpropoxy)-butyl, 4-(1 ,1 -dimethylethoxy)-butyl and the like.
The term "haloalkoxy-alkyl" as used herein denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. Examples are fluoromethoxymethyl, difluoro- methoxymethyl, trifluoromethoxymethyl, 1 -fluoroethoxymethyl, 2-fluoroethoxymethyl, 1 ,1 - difluoroethoxymethyl, 1 ,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1 ,1 ,2- trifluoroethoxymethyl, 1 ,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethox- ymethyl, 1 -fluoroethoxy-1 -ethyl, 2-fluoroethoxy-1 -ethyl, 1 ,1 -difluoroethoxy-1 -ethyl, 1 ,2- difluoroethoxy-1 -ethyl, 2,2-difluoroethoxy-1 -ethyl, 1 ,1 ,2-trifluoroethoxy-1 -ethyl, 1 ,2,2- trifluoroethoxy-1 -ethyl, 2,2,2-trifluoroethoxy-1 -ethyl, pentafluoroethoxy-1 -ethyl, 1 -fluoroethoxy-2- ethyl, 2-fluoroethoxy-2-ethyl, 1 ,1 -difluoroethoxy-2 -ethyl, 1 ,2-difluoroethoxy-2-ethyl, 2,2- difluoroethoxy-2-ethyl, 1 ,1 ,2-trifluoroethoxy-2-ethyl, 1 ,2,2-trifluoroethoxy-2-ethyl, 2,2,2- trifluoroethoxy-2-ethyl, pentafluoroethoxy-2-ethyl, and the like.
The term "alkylthio" (also alkylsulfanyl, "alkyl-S" or "alkyl-S(0)k" (wherein k is 0)) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms ("Ci-Cs-alkylthio"), frequently comprising 1 to 6 carbon atoms ("Ci-C6-alkylthio"), preferably 1 to 4 carbon atoms ("Ci-C4-alkylthio"), which is attached via a sulfur atom at any position in the alkyl group. Ci-C2-Alkylthio is methylthio or ethylthio. Ci-C4-Alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (iso- propylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 - dimethylethylthio (tert-butylthio). Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 - methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,1 ,2-trimethylpropylthio, 1 ,2,2- trimethylpropylthio, 1 -ethyl-1 -methylpropylthio or 1-ethyl-2-methylpropylthio. Ci-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
The term "haloalkylthio" as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine. Ci-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2CI, SCHCI2, SCC , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2- fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2- fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5. Ci-C4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,
2- chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio,
3- bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1 - (CH2F)-2-fluoroethylthio, 1 -(CH2CI)-2-chloroethylthio, 1 -(CH2Br)-2-bromoethylthio,
4- fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
5- iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio,
6- iodohexylthio or dodecafluorohexylthio.
The terms "alkylsulfinyl" and "alkyl-S(0)k" (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group. For exam- pie, the term "Ci-C2-alkylsulfinyl" refers to a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C4-alkylsulfinyl" refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C6-alkylsulfinyl" refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. Ci-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. Ci-C4-alkylsulfinyl is additionally, for example, n-propylsulfinyl,
1 -methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2- methylpropylsulfinyl (isobutylsulfinyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl). C1-C6- alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2- methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl,
2.2- dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2- methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 ,1 -dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl, 1 ,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,
2.3- dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1 -ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1 ,1 ,2- trimethylpropylsulfinyl, 1 ,2,2-trimethylpropylsulfinyl, 1 -ethyl-1 -methylpropylsulfinyl or 1 -ethyl-2- methylpropylsulfinyl.
The terms "alkylsulfonyl" and "alkyl-S(0)k" (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C2-alkylsulfonyl" refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C4-alkylsulfonyl" refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C6-alkylsulfonyl" refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. Ci-C2-alkylsulfonyl is methyl- sulfonyl or ethylsulfonyl. Ci-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec- butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert- butylsulfonyl). Ci-C6-alkylsulfonyl is additionally, for example, pentylsulfonyl,
1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 - methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl,
1 .1 - dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1 ,3-dimethylbutylsulfonyl,
2.2- dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,
1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1 ,1 ,2-trimethylpropylsulfonyl,
1 ,2,2-trimethylpropylsulfonyl, 1 -ethyl-1 -methylpropylsulfonyl or 1 -ethyl-2-methylpropylsulfonyl.
The term "alkylamino" as used herein denotes in each case a group R*HN-, wherein R* is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms ("Ci-Ce- alkylamino"), preferably 1 to 4 carbon atoms("Ci-C4-alkylamino"). Examples of Ci-C6-alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso- butylamino, tert-butylamino, and the like.
The term "dialkylamino" as used herein denotes in each case a group R*R°N-, wherein R* and R°, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms ("di-(Ci-C6-alkyl)-amino"), preferably 1 to 4 carbon atoms ("di- (Ci-C4-alkyl)-amino"). Examples of a di-(Ci-C6-alkyl)-amino group are dimethylamino, diethyla- mino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl- isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl- isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.
The suffix "-carbonyl" in a group denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C=0 group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl. The term "aryl" as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.
The term "het(ero)aryl" as used herein refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrim- idyl and the like.
The term "3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1 , 2, 3 or 4 heteroatoms as ring members selected from the groups consisting of N, O and S" as used herein denotes monocyclic or bicyclic radicals, the monocyclic or bicyclic radicals being saturated, unsaturated or aromatic where N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO2. An unsaturated heterocycle contains at least one C-C and/or C-N and/or N-N double bond(s). A fully unsaturated heterocycle contains as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the size(s) of the ring(s). An aromatic monocyclic heterocycle is a fully unsaturated 5- or 6-membered monocyclic heterocycle. An aromatic bicyclic heterocycle is an 8-, 9- or 10-membered bicyclic heterocycle consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring. The heterocycle may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle include:
oxirane-2-yl, aziridine-1 -yl, aziridine-2-yl, oxetan-2-yl, azetidine-1 -yl, azetidine-2-yl, azetidine-3- yl, thietane-1 -yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahy- drothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1 -yl, imidazolidin-2-yl, imidazoli- din-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxa- zolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1 ,2,4- oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-1 -yl,
1 ,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1 ,3-dioxan-5-yl, 1 ,4-dioxan-2-yl, piperidin-1 -yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl, hexahydro- pyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, pi- perazin-1 -yl, piperazin-2-yl, 1 ,3,5-hexahydrotriazin-1 -yl, 1 ,3,5-hexahydrotriazin-2-yl and
1 ,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1 -oxothiomorpholin-2-yl, 1 -oxothiomorpholin-3-yl, 1 - oxothiomorpholin-4-yl, 1 ,1 -dioxothiomorpholin-2-yl, 1 ,1 -dioxothiomorpholin-3-yl, 1 ,1 - dioxothiomorpholin-4-yl and the like.
Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3- yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2- isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3- dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-
4- yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-
4- yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydro- pyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrim- idinyl, di- or tetrahydropyrazinyl, 1 ,3, 5-di- or tetrahydrotriazin-2-yl and 1 ,2, 4-di- or tetrahydrotria- zin-3-yl.
A 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring is e.g. a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring. Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3- pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,
5- thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 2- pyridinyl, 3-pyridinyl, 4-pyridinyl, 1 -oxopyridin-2-yl, 1 -oxopyridin-3-yl, 1 -oxopyridin-4-yl,3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or
6- membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, ben- zimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, iso- chinolinyl, purinyl, 1 ,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.
If two radicals bound on the same nitrogen atom (for example Re and Rf or R2e and R2f or R9 and Rh or R¾ and R2h) together with the nitrogen atom, to which they are bound, form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N, this is for example pyrrolidine-1 -yl, pyrazolidin-1 -yl, imidazolidin-1 -yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin- 2-yl, [1 ,2,3]-triazolidin-1 -yl, [1 ,2,3]-triazolidin-2-yl, [1 ,2,4]-triazolidin-1 -yl, [1 ,2,4]-triazolidin-4-yl, [1 ,2,3]-oxadiazolidin-2-yl, [1 ,2,3]-oxadiazolidin-3-yl, [1 ,2,5]-oxadiazolidin-2-yl, [1 ,2,4]- oxadiazolidin-2-yl, [1 ,2,4]-oxadiazolidin-4-yl, [1 ,3,4]-oxadiazolidin-3-yl, [1 ,2,3]-thiadiazolidin-2-yl, [1 ,2,3]- thiadiazolidin-3-yl, [1 ,2,5]-thiadiazolidin-2-yl, [1 ,2,4]-thiadiazolidin-2-yl, [1 ,2,4]- thiadiazolidin-4-yl, [1 ,3,4]-thiadiazolidin-3-yl, piperdin-1 -yl, piperazine-1 -yl, morpholin-1 -yl, thio- morpholin-1 -yl, 1 -oxothiomorpholin-1 -yl, 1 ,1 -dioxothiomorpholin-1 -yl, azepan-1 -yl, 1 ,4-diazepan- 1 -yl, pyrrolin-1 -yl, pyrazolin-1 -yl, imidazolin-1 -yl, oxazolin-3-yl, isoxazolin-2-yl, thiazolin-3-yl, isothiazolin-1 -yl, 1 ,2-dihydropyridin-1 -yl, 1 ,2,3,4-tetrahydropyridin-1 -yl, 1 ,2,5,6-tetrahydropyridin- 1 -yl, 1 ,2-dihydropyridazin, 1 ,6-dihydropyridazin, 1 ,2,3,4-tetrahydropyridazin-1 -yl, 1 ,2,5,6- tetrahydropyridazin-1 -yl, 1 ,2-dihydropyrimidin, 1 ,6-dihydropyrimidin, 1 ,2,3,4-tetrahydropyrimidin- 1 -yl, 1 ,2,5,6-tetrahydropyrimidin-1 -yl, 1 ,2-dihydropyrazin-1 -yl, 1 ,2,3,4-tetrahydropyrazin-1 -yl, 1 ,2,5,6-tetrahydropyrazin-1 -yl, pyrrol-1 -yl, pyrazol-1 -yl, imidazol-1 -yl, [1 ,2,3]-1 H-triazol-1 -yl, [1 ,2,3]-2H-triazol-2-yl, [1 ,2,4]-1 H-triazol-1 -yl and [1 ,2,4]-4H-triazol-4-yl.
The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers, salts, tautomers or N-oxides thereof.
The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the compounds of formulae I, where applicable, as well as concerning the uses and methods according to the invention and the composition according to the invention.
Preferred compounds according to the invention are compounds of formula I or a stereoisomer, salt or N-oxide thereof, wherein the salt is an agriculturally suitable salt. Further preferred compounds according to the invention are compounds of formula I or an N-oxide or salt thereof, especially an agriculturally suitable salt. Particularly preferred compounds according to the invention are compounds of formula I or a salt thereof, especially an agriculturally suitable salt thereof.
According to one embodiment of the invention the variable X in the compounds of formula
I is N.
According to another embodiment of the invention the variable X in the compounds of formula I is CR2.
Preferred compounds according to the invention are compounds of formula I, wherein R1 is selected from the group consisting of CN, halogen, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, C1-C4- haloalkoxy-Ci-C4-alkoxy and R1b-S(0)k, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and C1-C4- haloalkyl. In this context Z1 is in particular a covalent bond.
More preferably, R1 is selected from halogen, CN, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C4-alkenyloxy, C3-C4-alkynyloxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- haloalkoxy-Ci-C4-alkoxy, Ci-C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0 or 2.
In particular, R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C3-C6- cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, specifically R1 is F, CI, Br, N02, CH3, cyclopropyl, CF3, OCH3, OCF3, SCF3, SO2CH3, CH2OCH3 or CH2OCH2CH2OCH3, and more specifically R1 is CI, N02, CH3, cyclopropyl, CF3, SO2CH3, CH2OCH3 or CH2OCH2CH2OCH3. In one group of embodiments of the invention, where X is CR2, the variable R2 is hydrogen.
In one group of embodiments of the invention, where X is CR2, the variable R2 of the compounds of formula I has any one of the meanings given above for R2 with the exception of hydrogen.
According to preferred embodiment of the invention the variable R2 in the compounds of formula I is a 5- or 6-membered heterocyclyl, where heterocyclyl is a saturated, partially unsaturated or aromatic heterocyclic radical, which contains as ring member 1 heteroatom selected from the group consisting of O, N and S and 0, 1 , 2 or 3 further nitrogen atom(s), where hetero- cyclyl is unsubstituted or carries 1 , 2 or 3 radicals R21, as defined herein, which are identical or different.
According to an even more preferred embodiment of the invention the variable R2 in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from the group consisting of isoxazolinyl (4,5-dihydroisoxazolyl), 1 ,2-dihydrotetrazolonyl, 1 ,4-dihydrotetrazolonyl, tetrahy- drofuryl, dioxolanyl, piperidinyl, morpholinyl, piperazinyl, isoxazolyl, pyrazolyl, thiazolyl, oxazolyl, furyl, pyridinyl, pyrimidinyl and pyrazinyl, where heterocyclyl is unsubstituted or carries 1 , 2 or 3 radicals R21 which are identical or different and are selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkylthio-Ci-C4-alkyl.
According to a particular embodiment of the invention the variable R2 in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from 4,5-dihydroisoxazol-3-yl, which is unsubstituted or substituted in position 5 with CH3, CH2F or CHF2, 4,5-dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH3, OCH3, CH2OCH3, CH2SCH3, 1 - methyl-5-oxo-1 ,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5-dihydrotetrazol-1 -yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3-methyl-isoxazol-5-yl, 1 -methyl-1 H-pyrazol- 3-yl, 2-methyl-2H-pyrazol-3-yl and thiazol-2-yl.
According to a preferred embodiment of the invention the variable R2 in the compounds of formula I is phenyl-Z2a, where Z2a is as defined herein, and where phenyl is unsubstituted or carries 1 , 2 or 3 radicals R21 which are identical or different and as defined above and which are in particular selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci- C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy, and preferably from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkyl and Ci-C2-alkoxy-Ci-C2-alkoxy.
According to a more preferred embodiment of the invention the variable R2 in the compounds of formula I is a radical of the following formula:
Figure imgf000019_0001
in which # denotes the bond through which the group R2 is attached and:
RP1 is hydrogen or halogen, preferably hydrogen, CI, Br or F, and in particular H or F; RP2 is hydrogen, halogen or Ci-C2-alkoxy, preferably hydrogen, CI, Br, F, OCH3 or OCH2CH3, and in particular H, F, CI or OCH3; and
RP3 is hydrogen, halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-alkoxy-Ci-C2- alkoxy, preferably hydrogen, CI, Br, F, CH3, C2H5, CF3, CHF2, CH2F, CCI2F, CF2CI, CH2CF3, CH2CHF2, CF2CF3, OCH3, OCH2CH3, OCH2OCH3, OCH2CH2OCH2CH3,
OCH2OCH2CH3 or OCH2CH2OCH3, and in particular is H, F, CI, CH3, CF3, OCH3,
OCH2CH3, OCH2OCH3 or OCH2CH2OCH3.
According to a particular embodiment of the invention the variable R2 in the compounds of formula I is phenyl which is unsubstituted or carries one radical R21 , where R21 is preferably at- tached to position 4 of the phenyl group and is as defined above and in particular selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkyl and Ci-C2-alkoxy-Ci-C2-alkoxy, preferably form CH3, C2H5, OCH3, OC2H5, CHF2, CF3, OCH2OCH3 and OCH2CH2OCH3, and specifically from OCH3
According to a preferred embodiment of the invention the variable R2 in the compounds of formula I is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl.
According to another preferred embodiment of the invention the variable R2 in the compounds of formula I is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6- haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkyl-S(0)k and C1-C4- haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl.
According to another preferred embodiment of the invention the variable R2 in the compounds of formula I is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl.
According to a more preferred embodiment of the invention the variable R2 in the compounds of formula I is selected from C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxy, C1-C2- haloalkoxy-Ci-C2-alkyl, C3-C4-alkenyloxy, C3-C4-alkynyloxy, Ci-C4-alkoxycarbonyl and C1-C4- alkyl-S(02), and in particular from CH=CH2, CH=CHCH3, CH2OCH2CF3, OC2H5, OCH2CH=CH2, OCH2C≡CH, C(0)OCH3, C(0)OC2H5, SO2CH3, S02C2H5 and S02CH(CH3)2. According to a specifically preferred embodiment of the invention the variable R2 in the compounds of formula I is selected from the group consisting of hydrogen, 4,5-dihydroisoxazol- 3-yl, which is unsubstituted or substituted in position 5 with CH3, CH2F or CHF2, 4,5- dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH3, OCH3, CH2OCH3, CH2SCH3, 1 -methyl-5-oxo-1 ,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5- dihydrotetrazol-1 -yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3- methyl-isoxazol-5-yl, 1 -methyl-1 H-pyrazol-3-yl, 2-methyl-2H-pyrazol-3-yl, thiazol-2-yl, 4-CH3- phenyl, 4-C2H5-phenyl, 4-OCH3-phenyl, 4-OC2H5-phenyl, 4-CHF2-phenyl, 4-CF3-phenyl, 4- OCH2OCH3-phenyl, 4-OCH2CH2OCH3-phenyl, CH=CH2, CH=CHCH3, CH2OCH2CF3, OC2H5, OCH2CH=CH2, OCH2C≡CH, C(0)OCH3, C(0)OC2H5, SO2CH3, S02C2H5 and S02CH(CH3)2, in particular selected from hydrogen, halogen, methyl, CH2OCH2CF3, methylsulfonyl, ethylsulfonyl, methylsulfanyl, ethylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 5-isoxazolinyl, 3-methyl-5- isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5-isoxazolyl, and specifically selected from hydrogen, chlorine, methylsulfonyl, methylsulfanyl, CH2OCH2CF3, 3- isoxazolinyl, 5-methyl-3-isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl and 3-methyl-5-isoxazolyl.
Preferred compounds according to the invention are compounds of formula I, wherein R3 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C4-alkenyloxy, C3- C4-alkynyloxy or R2b-S(0)k, where the variables k and R2b have one of the herein defined meanings.
More preferably, R3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkyl-S(0)2 and Ci-C4-haloalkyl-S(0)2.
In particular, R3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-
C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkylthio, Ci-C2-haloalkylthio, Ci-C2-alkyl-S(0)2 and Ci-C2-haloalkyl-S(0)2, specifically from H, CI, F, CN, N02, CH3, CF3, CHF2, OCH3, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(0)2CH3 and S(0)2CH2CH3, and more specifically from H, CI, F, CN, CH3, CF3 and S(0)2CH3.
Preferred compounds according to the invention are compounds of formula I, wherein R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl and C1-C2- haloalkyl, in particular from the group consisting of hydrogen, CHF2, CF3, CN, NO2, CH3 and halogen, and specifically from hydrogen, CHF2, CF3, CN, NO2, CH3, CI, Br and F.
Preferred compounds according to the invention are compounds of formula I, wherein R5 is selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, and in particular from the group consisting of CHF2, CF3 and halogen.
According to a particular embodiment of the invention R5 is chlorine or fluorine..
According to one embodiment of the invention, R6 in the compounds formula I is hydrogen. According to another embodiment of the invention, R6 in the compounds formula I is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, Ci-C6-cyano-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-haloalkoxy-Ci-C4-alkyl, RbRbN-S(0)n-Z, RbO-S(0)n-Z, Rb-S(0)n-Z,
Figure imgf000022_0001
, Rd-0-C(=0)0-Ci-C3-alkyl ,
Figure imgf000022_0002
phenyl-Z and where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups R', which are identical or different.
Preferred compounds according to the invention are compounds of formula I , wherein R6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci- C4-alkoxy-Ci-C4-alkyl, C3-C7-cycloalkyl, Ci-C4-haloalkyl, Rc-C(=0)-Ci-C2-alkyl,
Figure imgf000022_0003
C2-alkyl,
Figure imgf000022_0004
Rk-C(=0)NH-Ci-C2-alkyl and benzyl, where
Rc is Ci-C4-alkyl or Ci-C4-haloalkyl,
Rd is Ci-C4-alkyl,
Re is hydrogen or Ci-C4-alkyl,
Rf is hydrogen or Ci-C4-alkyl, or
Re, Rf together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7- membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 methyl groups,
Rk is Ci-C4-alkyl.
Further preferred compounds according to the invention are compounds of formula I, wherein R6 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl,
Figure imgf000022_0005
phenyl-Z and where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups R', which are identical or different.
Particularly preferred compounds according to the invention are compounds of formula I, wherein R6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci-C2-alkyl, particularly from hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2- ynyl, methoxycarbonylmethyl and benzyl.
Most preferred compounds according to the invention are compounds of formula I , wherein R6 is selected from the group consisting of hydrogen and Ci-C4-alkyl, particularly from hydro- gen, methyl and ethyl.
Preferred compounds according to the invention are compounds of formula I , wherein R7 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci- C4-alkoxy-Ci-C4-alkyl, C3-C7-cycloalkyl, Ci-C4-haloalkyl, Rc-C(=0)-Ci-C2-alkyl,
C2-alkyl,
Figure imgf000022_0006
Rk-C(=0)NH-Ci-C2-alkyl and benzyl, where
Rc is Ci-C4-alkyl or Ci-C4-haloalkyl, Rd is Ci-C4-alkyl,
Re is hydrogen or Ci-C4-alkyl,
Rf is hydrogen or Ci-C4-alkyl, or
Re, Rf together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7- membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 methyl groups,
Rk is Ci-C4-alkyl. Further preferred compounds according to the invention are compounds of formula I, wherein R7 is selected from the group consisting of Ci-C4-alkyl, C3-C7-cycloalkyl, Ci-C4-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy and Ci-C4-alkoxy-Ci-C4-alkyl.
Particularly preferred compounds according to the invention are compounds of formula I, wherein R7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy- Ci-C2-alkyl, particularly from methyl, ethyl, methoxy, ethoxy, n-propyl, methoxymethyl, ethox- ymethyl and methoxyethyl.
Most preferred compounds according to the invention are compounds of formula I, where- in R7 is selected from the group consisting methyl, ethyl, n-propyl and methoxyethyl.
In this context, the variables R', R11, R21, Z, Z , Z2, Z2a, Rb, R b, R2b, Rc, R2c, Rd, R2d, Re, R2e, Rf, R2f, R9, R¾, Rh, R2h, Rk, n and k, independently of each other, preferably have one of the following meanings:
R', R11, R21 independently of each other are selected from halogen, Ci-C4-alkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy and Ci-C6-haloalkyloxy, more preferably from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.
More preferably R', R11, R21 independently of each other are selected from the group con- sisting of halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; in particular selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkoxy- Ci-C4-alkoxy; and specifically from CI, F, Br, methyl, ethyl, methoxy and trifluoromethyl.
Z, Z1, Z2 independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.
Z2a is selected from a covalent bond, Ci-C2-alkanediyl, 0-Ci-C2-alkanediyl, C1-C2- alkanediyl-0 and Ci-C2-alkanediyl-0-Ci-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyI, O-ethanediyI, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.
Rb, R1b, R2b independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl,
Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy.
More preferably Rb,R1b, R2b independently of each other are selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
In particular, Rb, R1b, R2b independently of each other are selected from Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
Rc, R2c, Rk independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci- C4-alkoxy.
More preferably Rc, R2c, Rk independently of each other are selected from hydrogen, Ci-
C4-alkyl, Ci-C4-haloalkyl, C2-C-alkenyl, C2-C-haloalkenyl, C2-C-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
In particular, Rc, R2c, Rk independently of each other are selected from hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
Rd, R2d independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.
More preferably Rd, R2d independently of each other are selected from Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6- cycloalkyl. Re, Rf, R2e, R2f independently of each other are selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl and Ci-C4-alkoxy, or Re and Rf or R2e and R2f together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.
More preferably Re, Rf, R2e, R2f independently of each other are selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and benzyl, or Re and Rf or R2e and R2f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N- bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
In particular, Re, Rf, R2e, R2f independently of each other are selected from hydrogen and Ci-C4-alkyl, or Re and Rf or R2e and R2f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.
R9, R¾ independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl and benzyl.
More preferably Rs, R¾ independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl.
Rh, R2h independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl, benzyl and a radical C(=0)-Rk, where Rk is H, C1-C4- alkyl, Ci-C4-haloalkyl or phenyl.
More preferably Rh, R2h independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl; or
R9 and Rh or R¾ and R2h together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is
unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and Ci-C4-alkoxy;
more preferably Rs and Rh or R¾ and R2h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl;
and in particular, Rs and Rh or R¾ and R2h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.
n and k independently of each other are 0 or 2, and in particular 2.
Particularly preferred are compounds of formula I, wherein the variables R1 and R3 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, in particular from F, CI, Br, NO2,
CH3, cyclopropyl, CF3, OCH3, SCH3, OCF3, SCF3, SO2CH3, CH2OCH3 and CH2OCH2CH2OCH3; and
R3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and C1-C4- alkylsulfonyl, in particular from H, CI, F, CN, N02, CH3, CF3, CHF2, OCH3, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(0)2CH3 and S(0)2CH2CH3.
Especially preferred are compounds of formula I, where X is CR2 and the variables R1, R2, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci-
C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkyl-S(0)2;
R2 is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci- C4-alkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6- alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci- C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxa- zolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl;
R3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and
Ci-C4-alkyl-S(0)2; R4 is selected from the group consisting of hydrogen and halogen;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci- C2-alkyl;
R7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy-
Ci-C2-alkyl.
Also especially preferred are compounds of formula I, where X is CR2 and the variables R1 , R2, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkyl-S(0)2;
R2 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C2- alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy-Ci-C2-alkyl, Ci-C4-alkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be un- substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl;
R3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and Ci-C4-alkyl-S(0)2;
R4 is selected from the group consisting of hydrogen and halogen;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci-
C2-alkyl;
R7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy-
Ci-C2-alkyl.
Specifically preferred are compounds of formula I, where X is CR2 and the variables R1 , R2, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl;
R2 is selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methylsulfonyl, methylsulfinyl, methylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 5- isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5-isoxazolyl;
R3 is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl;
R4 is selected from the group consisting of hydrogen, chlorine and fluorine;R5is selected from the group consisting of chlorine and fluorine;
R6 is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl; R7 is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxyme- thyl, methoxyethyl and ethoxymethyl;
Especially preferred are compounds of formula I, where X is N and the variables R1, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci-
C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and
Ci-C4-alkyl-S(0)2;
R3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and Ci-C4-alkyl-S(0)2;
R4 is selected from the group consisting of hydrogen and halogen;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci- C2-alkyl;
R7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy- Ci-C2-alkyl.
Also specifically preferred are compounds of formula I, where X is N and the variables R1, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl;
R3 is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl;
R4 is selected from the group consisting of hydrogen, chlorine and fluorine;
R5 is selected from the group consisting of chlorine and fluorine;
R6 is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl;
R7 is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxyme- thyl, methoxyethyl and ethoxymethyl;
According to another preferred embodiment of the invention, where X is CR2, the variables R1, R2, R3, R4 and R5 together form one of the following substitution patterns on the phenyl ring of compounds of formula I, provided that position 1 is the attachment point of the phenyl ring to the remainder of the molecule:
2-Br-4,6-CI2, 2,6-CI2-4-CN, 2,4,6-C , 2,6-CI2-4-F, 2,6-CI2-4-CF3, 2,6-CI2-4-S(0)2CH3,
2-CF3-4-CN-6-CI, 2-CF3-4,6-CI2, 2-CF3-4-CF3-6-CI, 2-CF3-4-S(0)2CH3-6-CI,
2-CF3-4-F-6-CI, 2-CH3-CN-6-CI, 2-CH3-4,6-CI2, 2-CH3-4-CF3-6-CI,
2-CH3-4-S(0)2CH3-6-CI, 2-CH3-4-F-6-CI, 2-S(0)2CH3-4-CN-6-CI, 2-S(0)2CH3-4,6-CI2,
2-S(0)2CH3-4-CF3-6-CI, 2-S(0)2CH3-4-S(0)2CH3-6-CI, 2-S(0)2CH3-4-F-6-CI,
2-CI-4-CN-6-F, 2-CI-4-CF3-6-F, 2-CI-4-S(0)2CH3-6-F, 2,4-CI2-6-F, 2-CI-4,6-F2, 2-CF3-4-CN-6-F, 2-CF3-4-CF3-6-F, 2-CF3-4-S(0)2CH3-6-F, 2-CF3-4-CI-6-F,
2-CF3-4,6-F2, 2-CH3-4-CN-6-F, 2-CH3-4-CF3-6-F, 2-CH3-4-S(0)2CH3-6-F,
2-CH3-4-CI-6-F, 2-CH3-4,6-F2, 2-S(0)2CH3-4-CN-6-F, 2-S(0)2CH3-4-CF3-6-F,
2-S(0)2CH3-4-S(0)2CH3-6-F, 2-S(0)2CH3-4-CI-6-F, 2-S(0)2CH3-4,6-F2, 2,5-CI2-4-CN, 2,4,5-CI3, 2,5-CI2-4-F, 2,5-CI2-4-CF3, 2,5-CI2-4-S(0)2CH3, 2-CF3-4-CN-5-CI,
2-CF3-4,5-CI2, 2-CF3-4-CF3-5-CI, 2-CF3-4-S(0)2CH3-5-CI, 2-CF3-4-F-5-CI,
2-CH3-4-CN-5-CI, 2-CH3-4,5-CI2, 2-CH3-4-CF3-5-CI, 2-CH3-4-S(0)2CH3-5-CI,
2-CH3-4-F-5-CI, 2-S(0)2CH3-4-CN-5-CI, 2-S(0)2CH3-4,5-CI2, 2-S(0)2CH3-4-CF3-5-CI,
2-S(0)2CH3-4-S(0)2CH3-5-CI, 2-S(0)2CH3-4-F-5-CI, 2-CI-4-CN-5-F, 2-CI-4-CF3-5-F,
2-CI-4-S(0)2CH3-5-F, 2,4-CI2-5-F, 2-CI-4,5-F2, 2-CF3-4-CN-5-F, 2-CF3-4-CF3-5-F,
2-CF3-4-S(0)2CH3-5-F, 2-CF3-4-CI-5-F, 2-CF3-4,5-F2, 2-CH3-4-CN-5-F,
2-CH3-4-CF3-5-F, 2-CH3-4-S(0)2CH3-5-F, 2-CH3-4-CI-5-F, 2-CH3-4,5-F2,
2-S(0)2CH3-4-CN-5-F, 2-S(0)2CH3-4-CF3-5-F, 2-S(0)2CH3-4-S(0)2CH3-5-F,
2-S(0)2CH3-4-CI-5-F or 2-S(0)2CH3-4,5-F2.
According to another preferred embodiment of the invention the variables R1, R2, R3, R4 and R5 together form one of the following substitution patterns on the phenyl ring of compounds of formula I, provided that position 1 is the attachment point of the phenyl ring to the remainder of the molecule:
2,6-CI2-3-(3-isoxazolinyl)-4-CN, 2,4,6-CI3-3-(3-isoxazolinyl),
2,6-CI2-3-(3-isoxazolinyl)-4-F, 2,6-CI2-3-(3-isoxazolinyl)-4-CF3,
2,6-CI2-3-(3-isoxazolinyl)-4-S(0)2CH3, 2-CF3-3-(3-isoxazolinyl)-4-CN-6-CI, 2-CF3-3-(3- isoxazolinyl)-4,6-CI2, 2-CF3-3-(3-isoxazolinyl)-4-CF3-6-CI,
2-CF3-3-(3-isoxazolinyl)-4-S(0)2CH3-6-CI, 2-CF3-3-(3-isoxazolinyl)-4-F-6-CI,
2-CH3-3-(3-isoxazolinyl)-4-CN-6-CI, 2-CH3-3-(3-isoxazolinyl)-4,6-CI2,
2-CH3-3-(3-isoxazolinyl)-4-CF3-6-CI, 2-CH3-3-(3-isoxazolinyl)-4-S(0)2CH3-6-CI,
2-CH3-3-(3-isoxazolinyl)-4-F-6-CI, 2-S(0)2CH3-3-(3-isoxazolinyl)-4-CN-6-CI,
2-S(0)2CH3-3-(3-isoxazolinyl)-4,6-CI2, 2-S(0)2CH3-3-(3-isoxazolinyl)-4-CF3-6-CI,
2-S(0)2CH3-3-(3-isoxazolinyl)-4-S(0)2CH3-6-CI, 2-S(0)2CH3-3-(3-isoxazolinyl)-4-F-6-CI, 2-CI-3- (3-isoxazolinyl)-4-CN-6-F, 2-CI-3-(3-isoxazolinyl)-4-CF3-6-F,
2-CI-3-(3-isoxazolinyl)-4-S(0)2CH3-6-F,
2,4-CI2-3-(3-isoxazolinyl)-6-F, 2-CI-3-(3-isoxazolinyl)-4,6-F2,
2-CF3-3-(3-isoxazolinyl)-4-CN-6-F, 2-CF3-3-(3-isoxazolinyl)-4-CF3-6-F,
2-CF3-3-(3-isoxazolinyl)-4-S(0)2CH3-6-F, 2-CF3-3-(3-isoxazolinyl)-4-CI-6-F,
2-CF3-3-(3-isoxazolinyl)-4,6-F2, 2-CH3-3-(3-isoxazolinyl)-4-CN-6-F,
2-CH3-3-(3-isoxazolinyl)-4-CF3-6-F, 2-CH3-3-(3-isoxazolinyl)-4-S(0)2CH3-6-F,
2-CH3-3-(3-isoxazolinyl)-4-CI-6-F, 2-CH3-3-(3-isoxazolinyl)-4,6-F2,
2-S(0)2CH3-3-(3-isoxazolinyl)-4-CN-6-F, 2-S(0)2CH3-3-(3-isoxazolinyl)-4-CF3-6-F,
2-S(0)2CH3-3-(3-isoxazolinyl)-4-S(0)2CH3-6-F, 2-S(0)2CH3-3-(3-isoxazolinyl)-4-CI-6-F, 2- S(0)2CH3-3-(3-isoxazolinyl)-4,6-F2, 2,5-CI2-3-(3-isoxazolinyl)-4-CN,
2,6-CI2-3-(CH2-0-CH2CF3)-4-CN, 2,4,6-CI3-3-(3-isoxazolinyl),
2,6-CI2-3-(CH2-0-CH2CF3)-4-F, 2,6-CI2-3-(CH2-0-CH2CF3)-4-CF3, 2,6-Cl2-3-(CH2-0-CH2CF3)-4-S(0)2CH3, 2-CF3-3-(CH2-0-CH2CF3)-4-CN-6-CI,
2-CF3-3-(CH2-0-CH2CF3)-4,6-Cl2, 2-CF3-3-(CH2-0-CH2CF3)-4-CF3-6-CI,
2-CF3-3-(CH2-0-CH2CF3)-4-S(0)2CH3-6-CI, 2-CF3-3-(CH2-0-CH2CF3)-4-F-6-CI,
2-CH3-3-(CH2-0-CH2CF3)-4-CN-6-CI, 2-CH3-3-(CH2-0-CH2CF3)-4,6-CI2,
2-CH3-3-(CH2-0-CH2CF3)-4-CF3-6-CI, 2-CH3-3-(CH2-0-CH2CF3)-4-S(0)2CH3-6-CI,
2-CH3-3-( CH2-0-CH2CF3)-4-F-6-CI, 2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-CN-6-CI,
2-S(0)2CH3-3-(CH2-0-CH2CF3)-4,6-CI2, 2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-CF3-6-CI,
2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-S(0)2CH3-6-CI,
2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-F-6-CI, 2-CI-3-(CH2-0-CH2CF3)-4-CN-6-F,
2-CI-3-(CH2-0-CH2CF3)-4-CF3-6-F, 2-CI-3-(CH2-0-CH2CF3)-4-S(0)2CH3-6-F,
2,4-CI2-3-(CH2-0-CH2CF3)-6-F, 2-CI-3-(CH2-0-CH2CF3)-4,6-F2,
2-CF3-3-(CH2-0-CH2CF3)-4-CN-6-F, 2-CF3-3-(CH2-0-CH2CF3)-4-CF3-6-F,
2-CF3-3-(CH2-0-CH2CF3)-4-S(0)2CH3-6-F, 2-CF3-3-(CH2-0-CH2CF3)-4-CI-6-F,
2-CF3-3-(CH2-0-CH2CF3)-4,6-F2, 2-CH3-3-(CH2-0-CH2CF3)-4-CN-6-F,
2-CH3-3-(CH2-0-CH2CF3)-4-CF3-6-F, 2-CH3-3-(CH2-0-CH2CF3)-4-S(0)2CH3-6-F,
2-CH3-3-(CH2-0-CH2CF3)-4-CI-6-F, 2-CH3-3-(CH2-0-CH2CF3)-4,6-F2,
2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-CN-6-F, 2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-CF3-6-F,
2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-S(0)2CH3-6-F,
2-S(0)2CH3-3-(CH2-0-CH2CF3)-4-CI-6-F, 2-S(0)2CH3-3-(CH2-0-CH2CF3)-4,6-F2,
Examples of preferred compounds I.A, where X is N, are the individual compounds compiled in Tables 1 to 15 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment
Figure imgf000030_0001
Table 1 Compounds of formula I.A (I.A-1 .1 - I.A-1.2048) in which R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 2 Compounds of formula I.A (I.A-2.1 - II.A-2.2048) in which R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 3 Compounds of formula I.A (I.A-3.1 - I.A-3.2048) in which R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 4 Compounds of formula I.A (I.A-4.1 - I.A-4.2048) in which R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 5 Compounds of formula I .A (I.A-5.1 - I.A-5.2048) in which R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 6 Compounds of formula I .A (I.A-6.1 - I.A-6.2048) in which R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 7 Compounds of formula I .A (I.A-7.1 - I.A-7.2048) in which R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 8 Compounds of formula I .A (I.A-8.1 - I.A-8.2048) in which R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 9 Compounds of formula I .A (I.A-9.1 - I.A-9.2048) in which R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table l OCompounds of formula I.A (I.A-10.1 - I.A-10.2048) in which R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 1 Compounds of formula I.A (I.A-1 1.1 - I.A-1 1 .2048) in which R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 12Compounds of formula I.A (I.A-12.1 - I.A-12.2048) in which R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 13Compounds of formula I.A (I.A-13.1 - I.A-13.2048) in which R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 14Compounds of formula I.A (I.A-14.1 - I.A-14.2048) in which R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 15Compounds of formula I.A (I.A-15.1 - I.A-15.2048) in which R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table A
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
A-805 cyclopropyl F CH2CH3 CH3
A-806 cyclopropyl F CH2CH3 CH2CH3
A-807 cyclopropyl F CH2CH3 CH2CH2CH3
A-808 cyclopropyl F CH2CH3 CH2CH2OCH3
A-809 cyclopropyl F CH20CH3 CH3
A-810 cyclopropyl F CH20CH3 CH2CH3
A-81 1 cyclopropyl F CH20CH3 CH2CH2CH3
A-812 cyclopropyl F CH20CH3 CH2CH2OCH3
A-813 cyclopropyl F CH20CH2CH3 CH3
A-814 cyclopropyl F CH20CH2CH3 CH2CH3
A-815 cyclopropyl F CH20CH2CH3 CH2CH2CH3
A-816 cyclopropyl F CH20CH2CH3 CH2CH2OCH3
A-817 cyclopropyl F CH2(CO)OCH3 CH3
A-818 cyclopropyl F CH2(CO)OCH3 CH2CH3
A-819 cyclopropyl F CH2(CO)OCH3 CH2CH2CH3
A-820 cyclopropyl F CH2(CO)OCH3 CH2CH2OCH3
A-821 cyclopropyl F CH2CHCH2 CH3
A-822 cyclopropyl F CH2CHCH2 CH2CH3
A-823 cyclopropyl F CH2CHCH2 CH2CH2CH3
A-824 cyclopropyl F CH2CHCH2 CH2CH2OCH3
A-825 cyclopropyl F CH2CCH CH3
A-826 cyclopropyl F CH2CCH CH2CH3
A-827 cyclopropyl F CH2CCH CH2CH2CH3
A-828 cyclopropyl F CH2CCH CH2CH2OCH3
A-829 cyclopropyl F H CH3
A-830 cyclopropyl F H CH2CH3
A-831 cyclopropyl F H CH2CH2CH3
A-832 cyclopropyl F H CH2CH2OCH3
A-833 cyclopropyl CI CH3 CH3
A-834 cyclopropyl CI CH3 CH2CH3
A-835 cyclopropyl CI CH3 CH2CH2CH3
A-836 cyclopropyl CI CH3 CH2CH2OCH3
A-837 cyclopropyl CI CH2CH3 CH3
A-838 cyclopropyl CI CH2CH3 CH2CH3
A-839 cyclopropyl CI CH2CH3 CH2CH2CH3
A-840 cyclopropyl CI CH2CH3 CH2CH2OCH3
A-841 cyclopropyl CI CH2OCH3 CH3
A-842 cyclopropyl CI CH2OCH3 CH2CH3
A-843 cyclopropyl CI CH2OCH3 CH2CH2CH3
A-844 cyclopropyl CI CH2OCH3 CH2CH2OCH3 A-845 cyclopropyl CI CH2OCH2CH3 CH3
A-846 cyclopropyl CI CH2OCH2CH3 CH2CH3
A-847 cyclopropyl CI CH2OCH2CH3 CH2CH2CH3
A-848 cyclopropyl CI CH2OCH2CH3 CH2CH2OCH3
A-849 cyclopropyl CI CH2(CO)OCH3 CH3
A-850 cyclopropyl CI CH2(CO)OCH3 CH2CH3
A-851 cyclopropyl CI CH2(CO)OCH3 CH2CH2CH3
A-852 cyclopropyl CI CH2(CO)OCH3 CH2CH2OCH3
A-853 cyclopropyl CI CH2CHCH2 CH3
A-854 cyclopropyl CI CH2CHCH2 CH2CH3
A-855 cyclopropyl CI CH2CHCH2 CH2CH2CH3
A-856 cyclopropyl CI CH2CHCH2 CH2CH2OCH3
A-857 cyclopropyl CI CH2CCH CH3
A-858 cyclopropyl CI CH2CCH CH2CH3
A-859 cyclopropyl CI CH2CCH CH2CH2CH3
A-860 cyclopropyl CI CH2CCH CH2CH2OCH3
A-861 cyclopropyl CI H CH3
A-862 cyclopropyl CI H CH2CH3
A-863 cyclopropyl CI H CH2CH2CH3
A-864 cyclopropyl CI H CH2CH2OCH3
A-865 cyclopropyl Br CH3 CH3
A-866 cyclopropyl Br CH3 CH2CH3
A-867 cyclopropyl Br CH3 CH2CH2CH3
A-868 cyclopropyl Br CH3 CH2CH2OCH3
A-869 cyclopropyl Br CH2CH3 CH3
A-870 cyclopropyl Br CH2CH3 CH2CH3
A-871 cyclopropyl Br CH2CH3 CH2CH2CH3
A-872 cyclopropyl Br CH2CH3 CH2CH2OCH3
A-873 cyclopropyl Br CH2OCH3 CH3
A-874 cyclopropyl Br CH2OCH3 CH2CH3
A-875 cyclopropyl Br CH2OCH3 CH2CH2CH3
A-876 cyclopropyl Br CH2OCH3 CH2CH2OCH3
A-877 cyclopropyl Br CH2OCH2CH3 CH3
A-878 cyclopropyl Br CH2OCH2CH3 CH2CH3
A-879 cyclopropyl Br CH2OCH2CH3 CH2CH2CH3
A-880 cyclopropyl Br CH2OCH2CH3 CH2CH2OCH3
A-881 cyclopropyl Br CH2(CO)OCH3 CH3
A-882 cyclopropyl Br CH2(CO)OCH3 CH2CH3
A-883 cyclopropyl Br CH2(CO)OCH3 CH2CH2CH3
A-884 cyclopropyl Br CH2(CO)OCH3 CH2CH2OCH3 A-885 cyclopropyl Br CH2CHCH2 CHs
A-886 cyclopropyl Br CH2CHCH2 CH2CH3
A-887 cyclopropyl Br CH2CHCH2 CH2CH2CH3
A-888 cyclopropyl Br CH2CHCH2 CH2CH2OCH3
A-889 cyclopropyl Br CH2CCH CHs
A-890 cyclopropyl Br CH2CCH CH2CH3
A-891 cyclopropyl Br CH2CCH CH2CH2CH3
A-892 cyclopropyl Br CH2CCH CH2CH2OCH3
A-893 cyclopropyl Br H CHs
A-894 cyclopropyl Br H CH2CH3
A-895 cyclopropyl Br H CH2CH2CH3
A-896 cyclopropyl Br H CH2CH2OCH3
A-897 cyclopropyl CN CHs CHs
A-898 cyclopropyl CN CHs CH2CH3
A-899 cyclopropyl CN CHs CH2CH2CH3
A-900 cyclopropyl CN CHs CH2CH2OCH3
A-901 cyclopropyl CN CH2CH3 CHs
A-902 cyclopropyl CN CH2CH3 CH2CH3
A-903 cyclopropyl CN CH2CH3 CH2CH2CH3
A-904 cyclopropyl CN CH2CH3 CH2CH2OCH3
A-905 cyclopropyl CN CH2OCH3 CHs
A-906 cyclopropyl CN CH2OCH3 CH2CH3
A-907 cyclopropyl CN CH2OCH3 CH2CH2CH3
A-908 cyclopropyl CN CH2OCH3 CH2CH2OCH3
A-909 cyclopropyl CN CH2OCH2CH3 CHs
A-910 cyclopropyl CN CH2OCH2CH3 CH2CH3
A-91 1 cyclopropyl CN CH2OCH2CH3 CH2CH2CH3
A-912 cyclopropyl CN CH2OCH2CH3 CH2CH2OCH3
A-913 cyclopropyl CN CH2(CO)OCH3 CHs
A-914 cyclopropyl CN CH2(CO)OCHs CH2CH3
A-915 cyclopropyl CN CH2(CO)OCH3 CH2CH2CH3
A-916 cyclopropyl CN CH2(CO)OCHs CH2CH2OCH3
A-917 cyclopropyl CN CH2CHCH2 CHs
A-918 cyclopropyl CN CH2CHCH2 CH2CH3
A-919 cyclopropyl CN CH2CHCH2 CH2CH2CH3
A-920 cyclopropyl CN CH2CHCH2 CH2CH2OCH3
A-921 cyclopropyl CN CH2CCH CHs
A-922 cyclopropyl CN CH2CCH CH2CH3
A-923 cyclopropyl CN CH2CCH CH2CH2CH3
A-924 cyclopropyl CN CH2CCH CH2CH2OCH3 A-925 cyclopropyl CN H CHs
A-926 cyclopropyl CN H CH2CH3
A-927 cyclopropyl CN H CH2CH2CH3
A-928 cyclopropyl CN H CH2CH2OCH3
A-929 cyclopropyl CHs CHs CHs
A-930 cyclopropyl CHs CHs CH2CH3
A-931 cyclopropyl CHs CHs CH2CH2CH3
A-932 cyclopropyl CHs CHs CH2CH2OCH3
A-933 cyclopropyl CHs CH2CH3 CHs
A-934 cyclopropyl CHs CH2CH3 CH2CH3
A-935 cyclopropyl CHs CH2CH3 CH2CH2CH3
A-936 cyclopropyl CHs CH2CH3 CH2CH2OCH3
A-937 cyclopropyl CHs CH2OCH3 CHs
A-938 cyclopropyl CHs CH2OCH3 CH2CH3
A-939 cyclopropyl CHs CH2OCH3 CH2CH2CH3
A-940 cyclopropyl CHs CH2OCH3 CH2CH2OCH3
A-941 cyclopropyl CHs CH2OCH2CH3 CHs
A-942 cyclopropyl CHs CH2OCH2CH3 CH2CH3
A-943 cyclopropyl CHs CH2OCH2CH3 CH2CH2CH3
A-944 cyclopropyl CHs CH2OCH2CH3 CH2CH2OCH3
A-945 cyclopropyl CHs CH2(CO)OCH3 CHs
A-946 cyclopropyl CHs CH2(CO)OCHs CH2CH3
A-947 cyclopropyl CHs CH2(CO)OCH3 CH2CH2CH3
A-948 cyclopropyl CHs CH2(CO)OCHs CH2CH2OCH3
A-949 cyclopropyl CHs CH2CHCH2 CHs
A-950 cyclopropyl CHs CH2CHCH2 CH2CH3
A-951 cyclopropyl CHs CH2CHCH2 CH2CH2CH3
A-952 cyclopropyl CHs CH2CHCH2 CH2CH2OCH3
A-953 cyclopropyl CHs CH2CCH CHs
A-954 cyclopropyl CHs CH2CCH CH2CH3
A-955 cyclopropyl CHs CH2CCH CH2CH2CH3
A-956 cyclopropyl CHs CH2CCH CH2CH2OCH3
A-957 cyclopropyl CHs H CHs
A-958 cyclopropyl CHs H CH2CH3
A-959 cyclopropyl CHs H CH2CH2CH3
A-960 cyclopropyl CHs H CH2CH2OCH3
A-961 cyclopropyl CFs CHs CHs
A-962 cyclopropyl CFs CHs CH2CH3
A-963 cyclopropyl CFs CHs CH2CH2CH3
A-964 cyclopropyl CFs CHs CH2CH2OCH3 A-965 cyclopropyl CFs CH2CH3 CHs
A-966 cyclopropyl CFs CH2CH3 CH2CH3
A-967 cyclopropyl CFs CH2CH3 CH2CH2CH3
A-968 cyclopropyl CFs CH2CH3 CH2CH2OCH3
A-969 cyclopropyl CFs CH2OCH3 CHs
A-970 cyclopropyl CFs CH2OCH3 CH2CH3
A-971 cyclopropyl CFs CH2OCH3 CH2CH2CH3
A-972 cyclopropyl CFs CH2OCH3 CH2CH2OCH3
A-973 cyclopropyl CFs CH2OCH2CH3 CHs
A-974 cyclopropyl CFs CH2OCH2CH3 CH2CH3
A-975 cyclopropyl CFs CH2OCH2CH3 CH2CH2CH3
A-976 cyclopropyl CFs CH2OCH2CH3 CH2CH2OCH3
A-977 cyclopropyl CFs CH2(CO)OCHs CHs
A-978 cyclopropyl CFs CH2(CO)OCH3 CH2CH3
A-979 cyclopropyl CFs CH2(CO)OCHs CH2CH2CH3
A-980 cyclopropyl CFs CH2(CO)OCH3 CH2CH2OCH3
A-981 cyclopropyl CFs CH2CHCH2 CHs
A-982 cyclopropyl CFs CH2CHCH2 CH2CH3
A-983 cyclopropyl CFs CH2CHCH2 CH2CH2CH3
A-984 cyclopropyl CFs CH2CHCH2 CH2CH2OCH3
A-985 cyclopropyl CFs CH2CCH CHs
A-986 cyclopropyl CFs CH2CCH CH2CH3
A-987 cyclopropyl CFs CH2CCH CH2CH2CH3
A-988 cyclopropyl CFs CH2CCH CH2CH2OCH3
A-989 cyclopropyl CFs H CHs
A-990 cyclopropyl CFs H CH2CH3
A-991 cyclopropyl CFs H CH2CH2CH3
A-992 cyclopropyl CFs H CH2CH2OCH3
A-993 cyclopropyl SO2CH3 CHs CHs
A-994 cyclopropyl SO2CH3 CHs CH2CH3
A-995 cyclopropyl SO2CH3 CHs CH2CH2CH3
A-996 cyclopropyl SO2CH3 CHs CH2CH2OCH3
A-997 cyclopropyl SO2CH3 CH2CH3 CHs
A-998 cyclopropyl SO2CH3 CH2CH3 CH2CH3
A-999 cyclopropyl SO2CH3 CH2CH3 CH2CH2CH3
A-1000 cyclopropyl SO2CH3 CH2CH3 CH2CH2OCH3
A-1001 cyclopropyl SO2CH3 CH2OCH3 CHs
A-1002 cyclopropyl SO2CH3 CH2OCH3 CH2CH3
A-1003 cyclopropyl SO2CH3 CH2OCH3 CH2CH2CH3
A-1004 cyclopropyl SO2CH3 CH2OCH3 CH2CH2OCH3
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
A-1285 CH2OCH2CH2OCH3 H CH2CH3 CH3
A-1286 CH2OCH2CH2OCH3 H CH2CH3 CH2CH3
A-1287 CH2OCH2CH2OCH3 H CH2CH3 CH2CH2CH3
A-1288 CH2OCH2CH2OCH3 H CH2CH3 CH2CH2OCH3
A-1289 CH2OCH2CH2OCH3 H CH2OCH3 CH3
A-1290 CH2OCH2CH2OCH3 H CH2OCH3 CH2CH3
A-1291 CH2OCH2CH2OCH3 H CH2OCH3 CH2CH2CH3
A-1292 CH2OCH2CH2OCH3 H CH2OCH3 CH2CH2OCH3
A-1293 CH2OCH2CH2OCH3 H CH2OCH2CH3 CH3
A-1294 CH2OCH2CH2OCH3 H CH2OCH2CH3 CH2CH3
A-1295 CH2OCH2CH2OCH3 H CH2OCH2CH3 CH2CH2CH3
A-1296 CH2OCH2CH2OCH3 H CH2OCH2CH3 CH2CH2OCH3
A-1297 CH2OCH2CH2OCH3 H CH2(CO)OCH3 CH3
A-1298 CH2OCH2CH2OCH3 H CH2(CO)OCH3 CH2CH3
A-1299 CH2OCH2CH2OCH3 H CH2(CO)OCH3 CH2CH2CH3
A-1300 CH2OCH2CH2OCH3 H CH2(CO)OCH3 CH2CH2OCH3
A-1301 CH2OCH2CH2OCH3 H CH2CHCH2 CH3
A-1302 CH2OCH2CH2OCH3 H CH2CHCH2 CH2CH3
A-1303 CH2OCH2CH2OCH3 H CH2CHCH2 CH2CH2CH3
A-1304 CH2OCH2CH2OCH3 H CH2CHCH2 CH2CH2OCH3
A-1305 CH2OCH2CH2OCH3 H CH2CCH CH3
A-1306 CH2OCH2CH2OCH3 H CH2CCH CH2CH3
A-1307 CH2OCH2CH2OCH3 H CH2CCH CH2CH2CH3
A-1308 CH2OCH2CH2OCH3 H CH2CCH CH2CH2OCH3
A-1309 CH2OCH2CH2OCH3 H H CH3
A-1310 CH2OCH2CH2OCH3 H H CH2CH3
A-131 1 CH2OCH2CH2OCH3 H H CH2CH2CH3
A-1312 CH2OCH2CH2OCH3 H H CH2CH2OCH3
A-1313 CH2OCH2CH2OCH3 F CH3 CH3
A-1314 CH2OCH2CH2OCH3 F CH3 CH2CH3
A-1315 CH2OCH2CH2OCH3 F CH3 CH2CH2CH3
A-1316 CH2OCH2CH2OCH3 F CH3 CH2CH2OCH3
A-1317 CH2OCH2CH2OCH3 F CH2CH3 CH3
A-1318 CH2OCH2CH2OCH3 F CH2CH3 CH2CH3
A-1319 CH2OCH2CH2OCH3 F CH2CH3 CH2CH2CH3
A-1320 CH2OCH2CH2OCH3 F CH2CH3 CH2CH2OCH3
A-1321 CH2OCH2CH2OCH3 F CH2OCH3 CH3
A-1322 CH2OCH2CH2OCH3 F CH2OCH3 CH2CH3
A-1323 CH2OCH2CH2OCH3 F CH2OCH3 CH2CH2CH3
A-1324 CH2OCH2CH2OCH3 F CH2OCH3 CH2CH2OCH3 A-1325 CH2OCH2CH2OCH3 F CH20CH2CH3 CH3
A-1326 CH2OCH2CH2OCH3 F CH20CH2CH3 CH2CH3
A-1327 CH2OCH2CH2OCH3 F CH20CH2CH3 CH2CH2CH3
A-1328 CH2OCH2CH2OCH3 F CH20CH2CH3 CH2CH2OCH3
A-1329 CH2OCH2CH2OCH3 F CH2(CO)OCH3 CH3
A-1330 CH2OCH2CH2OCH3 F CH2(CO)OCH3 CH2CH3
A-1331 CH2OCH2CH2OCH3 F CH2(CO)OCH3 CH2CH2CH3
A-1332 CH2OCH2CH2OCH3 F CH2(CO)OCH3 CH2CH2OCH3
A-1333 CH2OCH2CH2OCH3 F CH2CHCH2 CH3
A-1334 CH2OCH2CH2OCH3 F CH2CHCH2 CH2CH3
A-1335 CH2OCH2CH2OCH3 F CH2CHCH2 CH2CH2CH3
A-1336 CH2OCH2CH2OCH3 F CH2CHCH2 CH2CH2OCH3
A-1337 CH2OCH2CH2OCH3 F CH2CCH CH3
A-1338 CH2OCH2CH2OCH3 F CH2CCH CH2CH3
A-1339 CH2OCH2CH2OCH3 F CH2CCH CH2CH2CH3
A-1340 CH2OCH2CH2OCH3 F CH2CCH CH2CH2OCH3
A-1341 CH2OCH2CH2OCH3 F H CH3
A-1342 CH2OCH2CH2OCH3 F H CH2CH3
A-1343 CH2OCH2CH2OCH3 F H CH2CH2CH3
A-1344 CH2OCH2CH2OCH3 F H CH2CH2OCH3
A-1345 CH2OCH2CH2OCH3 CI CH3 CH3
A-1346 CH2OCH2CH2OCH3 CI CH3 CH2CH3
A-1347 CH2OCH2CH2OCH3 CI CH3 CH2CH2CH3
A-1348 CH2OCH2CH2OCH3 CI CH3 CH2CH2OCH3
A-1349 CH2OCH2CH2OCH3 CI CH2CH3 CH3
A-1350 CH2OCH2CH2OCH3 CI CH2CH3 CH2CH3
A-1351 CH2OCH2CH2OCH3 CI CH2CH3 CH2CH2CH3
A-1352 CH2OCH2CH2OCH3 CI CH2CH3 CH2CH2OCH3
A-1353 CH2OCH2CH2OCH3 CI CH2OCH3 CH3
A-1354 CH2OCH2CH2OCH3 CI CH2OCH3 CH2CH3
A-1355 CH2OCH2CH2OCH3 CI CH2OCH3 CH2CH2CH3
A-1356 CH2OCH2CH2OCH3 CI CH2OCH3 CH2CH2OCH3
A-1357 CH2OCH2CH2OCH3 CI CH2OCH2CH3 CH3
A-1358 CH2OCH2CH2OCH3 CI CH2OCH2CH3 CH2CH3
A-1359 CH2OCH2CH2OCH3 CI CH2OCH2CH3 CH2CH2CH3
A-1360 CH2OCH2CH2OCH3 CI CH2OCH2CH3 CH2CH2OCH3
A-1361 CH2OCH2CH2OCH3 CI CH2(CO)OCH3 CH3
A-1362 CH2OCH2CH2OCH3 CI CH2(CO)OCH3 CH2CH3
A-1363 CH2OCH2CH2OCH3 CI CH2(CO)OCH3 CH2CH2CH3
A-1364 CH2OCH2CH2OCH3 CI CH2(CO)OCH3 CH2CH2OCH3 A-1365 CH2OCH2CH2OCH3 CI CH2CHCH2 CH3
A-1366 CH2OCH2CH2OCH3 CI CH2CHCH2 CH2CH3
A-1367 CH2OCH2CH2OCH3 CI CH2CHCH2 CH2CH2CH3
A-1368 CH2OCH2CH2OCH3 CI CH2CHCH2 CH2CH2OCH3
A-1369 CH2OCH2CH2OCH3 CI CH2CCH CH3
A-1370 CH2OCH2CH2OCH3 CI CH2CCH CH2CH3
A-1371 CH2OCH2CH2OCH3 CI CH2CCH CH2CH2CH3
A-1372 CH2OCH2CH2OCH3 CI CH2CCH CH2CH2OCH3
A-1373 CH2OCH2CH2OCH3 CI H CH3
A-1374 CH2OCH2CH2OCH3 CI H CH2CH3
A-1375 CH2OCH2CH2OCH3 CI H CH2CH2CH3
A-1376 CH2OCH2CH2OCH3 CI H CH2CH2OCH3
A-1377 CH2OCH2CH2OCH3 Br CH3 CH3
A-1378 CH2OCH2CH2OCH3 Br CH3 CH2CH3
A-1379 CH2OCH2CH2OCH3 Br CH3 CH2CH2CH3
A-1380 CH2OCH2CH2OCH3 Br CH3 CH2CH2OCH3
A-1381 CH2OCH2CH2OCH3 Br CH2CH3 CH3
A-1382 CH2OCH2CH2OCH3 Br CH2CH3 CH2CH3
A-1383 CH2OCH2CH2OCH3 Br CH2CH3 CH2CH2CH3
A-1384 CH2OCH2CH2OCH3 Br CH2CH3 CH2CH2OCH3
A-1385 CH2OCH2CH2OCH3 Br CH2OCH3 CH3
A-1386 CH2OCH2CH2OCH3 Br CH2OCH3 CH2CH3
A-1387 CH2OCH2CH2OCH3 Br CH2OCH3 CH2CH2CH3
A-1388 CH2OCH2CH2OCH3 Br CH2OCH3 CH2CH2OCH3
A-1389 CH2OCH2CH2OCH3 Br CH2OCH2CH3 CH3
A-1390 CH2OCH2CH2OCH3 Br CH2OCH2CH3 CH2CH3
A-1391 CH2OCH2CH2OCH3 Br CH2OCH2CH3 CH2CH2CH3
A-1392 CH2OCH2CH2OCH3 Br CH2OCH2CH3 CH2CH2OCH3
A-1393 CH2OCH2CH2OCH3 Br CH2(CO)OCH3 CH3
A-1394 CH2OCH2CH2OCH3 Br CH2(CO)OCH3 CH2CH3
A-1395 CH2OCH2CH2OCH3 Br CH2(CO)OCH3 CH2CH2CH3
A-1396 CH2OCH2CH2OCH3 Br CH2(CO)OCH3 CH2CH2OCH3
A-1397 CH2OCH2CH2OCH3 Br CH2CHCH2 CH3
A-1398 CH2OCH2CH2OCH3 Br CH2CHCH2 CH2CH3
A-1399 CH2OCH2CH2OCH3 Br CH2CHCH2 CH2CH2CH3
A-1400 CH2OCH2CH2OCH3 Br CH2CHCH2 CH2CH2OCH3
A-1401 CH2OCH2CH2OCH3 Br CH2CCH CH3
A-1402 CH2OCH2CH2OCH3 Br CH2CCH CH2CH3
A-1403 CH2OCH2CH2OCH3 Br CH2CCH CH2CH2CH3
A-1404 CH2OCH2CH2OCH3 Br CH2CCH CH2CH2OCH3 A-1405 CH2OCH2CH2OCH3 Br H CH3
A-1406 CH2OCH2CH2OCH3 Br H CH2CH3
A-1407 CH2OCH2CH2OCH3 Br H CH2CH2CH3
A-1408 CH2OCH2CH2OCH3 Br H CH2CH2OCH3
A-1409 CH2OCH2CH2OCH3 CN CH3 CH3
A-1410 CH2OCH2CH2OCH3 CN CH3 CH2CH3
A-141 1 CH2OCH2CH2OCH3 CN CH3 CH2CH2CH3
A-1412 CH2OCH2CH2OCH3 CN CH3 CH2CH2OCH3
A-1413 CH2OCH2CH2OCH3 CN CH2CH3 CH3
A-1414 CH2OCH2CH2OCH3 CN CH2CH3 CH2CH3
A-1415 CH2OCH2CH2OCH3 CN CH2CH3 CH2CH2CH3
A-1416 CH2OCH2CH2OCH3 CN CH2CH3 CH2CH2OCH3
A-1417 CH2OCH2CH2OCH3 CN CH2OCH3 CH3
A-1418 CH2OCH2CH2OCH3 CN CH2OCH3 CH2CH3
A-1419 CH2OCH2CH2OCH3 CN CH2OCH3 CH2CH2CH3
A-1420 CH2OCH2CH2OCH3 CN CH2OCH3 CH2CH2OCH3
A-1421 CH2OCH2CH2OCH3 CN CH2OCH2CH3 CH3
A-1422 CH2OCH2CH2OCH3 CN CH2OCH2CH3 CH2CH3
A-1423 CH2OCH2CH2OCH3 CN CH2OCH2CH3 CH2CH2CH3
A-1424 CH2OCH2CH2OCH3 CN CH2OCH2CH3 CH2CH2OCH3
A-1425 CH2OCH2CH2OCH3 CN CH2(CO)OCH3 CH3
A-1426 CH2OCH2CH2OCH3 CN CH2(CO)OCH3 CH2CH3
A-1427 CH2OCH2CH2OCH3 CN CH2(CO)OCH3 CH2CH2CH3
A-1428 CH2OCH2CH2OCH3 CN CH2(CO)OCH3 CH2CH2OCH3
A-1429 CH2OCH2CH2OCH3 CN CH2CHCH2 CH3
A-1430 CH2OCH2CH2OCH3 CN CH2CHCH2 CH2CH3
A-1431 CH2OCH2CH2OCH3 CN CH2CHCH2 CH2CH2CH3
A-1432 CH2OCH2CH2OCH3 CN CH2CHCH2 CH2CH2OCH3
A-1433 CH2OCH2CH2OCH3 CN CH2CCH CH3
A-1434 CH2OCH2CH2OCH3 CN CH2CCH CH2CH3
A-1435 CH2OCH2CH2OCH3 CN CH2CCH CH2CH2CH3
A-1436 CH2OCH2CH2OCH3 CN CH2CCH CH2CH2OCH3
A-1437 CH2OCH2CH2OCH3 CN H CH3
A-1438 CH2OCH2CH2OCH3 CN H CH2CH3
A-1439 CH2OCH2CH2OCH3 CN H CH2CH2CH3
A-1440 CH2OCH2CH2OCH3 CN H CH2CH2OCH3
A-1441 CH2OCH2CH2OCH3 CH3 CH3 CH3
A-1442 CH2OCH2CH2OCH3 CH3 CH3 CH2CH3
A-1443 CH2OCH2CH2OCH3 CH3 CH3 CH2CH2CH3
A-1444 CH2OCH2CH2OCH3 CH3 CH3 CH2CH2OCH3 A-1445 CH2OCH2CH2OCH3 CH3 CH2CH3 CH3
A-1446 CH2OCH2CH2OCH3 CH3 CH2CH3 CH2CH3
A-1447 CH2OCH2CH2OCH3 CH3 CH2CH3 CH2CH2CH3
A-1448 CH2OCH2CH2OCH3 CH3 CH2CH3 CH2CH2OCH3
A-1449 CH2OCH2CH2OCH3 CH3 CH2OCH3 CH3
A-1450 CH2OCH2CH2OCH3 CH3 CH2OCH3 CH2CH3
A-1451 CH2OCH2CH2OCH3 CH3 CH2OCH3 CH2CH2CH3
A-1452 CH2OCH2CH2OCH3 CH3 CH2OCH3 CH2CH2OCH3
A-1453 CH2OCH2CH2OCH3 CH3 CH2OCH2CH3 CH3
A-1454 CH2OCH2CH2OCH3 CH3 CH2OCH2CH3 CH2CH3
A- 1455 CH2OCH2CH2OCH3 CH3 CH2OCH2CH3 CH2CH2CH3
A-1456 CH2OCH2CH2OCH3 CH3 CH2OCH2CH3 CH2CH2OCH3
A-1457 CH2OCH2CH2OCH3 CH3 CH2(CO)OCH3 CH3
A-1458 CH2OCH2CH2OCH3 CH3 CH2(CO)OCH3 CH2CH3
A-1459 CH2OCH2CH2OCH3 CH3 CH2(CO)OCH3 CH2CH2CH3
A-1460 CH2OCH2CH2OCH3 CH3 CH2(CO)OCH3 CH2CH2OCH3
A-1461 CH2OCH2CH2OCH3 CH3 CH2CHCH2 CH3
A-1462 CH2OCH2CH2OCH3 CH3 CH2CHCH2 CH2CH3
A-1463 CH2OCH2CH2OCH3 CH3 CH2CHCH2 CH2CH2CH3
A-1464 CH2OCH2CH2OCH3 CH3 CH2CHCH2 CH2CH2OCH3
A-1465 CH2OCH2CH2OCH3 CH3 CH2CCH CH3
A-1466 CH2OCH2CH2OCH3 CH3 CH2CCH CH2CH3
A-1467 CH2OCH2CH2OCH3 CH3 CH2CCH CH2CH2CH3
A-1468 CH2OCH2CH2OCH3 CH3 CH2CCH CH2CH2OCH3
A-1469 CH2OCH2CH2OCH3 CH3 H CH3
A-1470 CH2OCH2CH2OCH3 CH3 H CH2CH3
A-1471 CH2OCH2CH2OCH3 CH3 H CH2CH2CH3
A-1472 CH2OCH2CH2OCH3 CH3 H CH2CH2OCH3
A-1473 CH2OCH2CH2OCH3 CF3 CH3 CH3
A-1474 CH2OCH2CH2OCH3 CF3 CH3 CH2CH3
A-1475 CH2OCH2CH2OCH3 CF3 CH3 CH2CH2CH3
A-1476 CH2OCH2CH2OCH3 CF3 CH3 CH2CH2OCH3
A-1477 CH2OCH2CH2OCH3 CF3 CH2CH3 CH3
A-1478 CH2OCH2CH2OCH3 CF3 CH2CH3 CH2CH3
A-1479 CH2OCH2CH2OCH3 CF3 CH2CH3 CH2CH2CH3
A-1480 CH2OCH2CH2OCH3 CF3 CH2CH3 CH2CH2OCH3
A-1481 CH2OCH2CH2OCH3 CF3 CH2OCH3 CH3
A-1482 CH2OCH2CH2OCH3 CF3 CH2OCH3 CH2CH3
A-1483 CH2OCH2CH2OCH3 CF3 CH2OCH3 CH2CH2CH3
A-1484 CH2OCH2CH2OCH3 CF3 CH2OCH3 CH2CH2OCH3 A-1485 CH2OCH2CH2OCH3 CF3 CH2OCH2CH3 CH3
A-1486 CH2OCH2CH2OCH3 CF3 CH2OCH2CH3 CH2CH3
A-1487 CH2OCH2CH2OCH3 CF3 CH2OCH2CH3 CH2CH2CH3
A-1488 CH2OCH2CH2OCH3 CF3 CH2OCH2CH3 CH2CH2OCH3
A-1489 CH2OCH2CH2OCH3 CF3 CH2(CO)OCH3 CH3
A-1490 CH2OCH2CH2OCH3 CF3 CH2(CO)OCH3 CH2CH3
A-1491 CH2OCH2CH2OCH3 CF3 CH2(CO)OCH3 CH2CH2CH3
A-1492 CH2OCH2CH2OCH3 CF3 CH2(CO)OCH3 CH2CH2OCH3
A-1493 CH2OCH2CH2OCH3 CF3 CH2CHCH2 CH3
A-1494 CH2OCH2CH2OCH3 CF3 CH2CHCH2 CH2CH3
A-1495 CH2OCH2CH2OCH3 CF3 CH2CHCH2 CH2CH2CH3
A-1496 CH2OCH2CH2OCH3 CF3 CH2CHCH2 CH2CH2OCH3
A-1497 CH2OCH2CH2OCH3 CF3 CH2CCH CH3
A-1498 CH2OCH2CH2OCH3 CF3 CH2CCH CH2CH3
A-1499 CH2OCH2CH2OCH3 CF3 CH2CCH CH2CH2CH3
A-1500 CH2OCH2CH2OCH3 CF3 CH2CCH CH2CH2OCH3
A-1501 CH2OCH2CH2OCH3 CF3 H CH3
A-1502 CH2OCH2CH2OCH3 CF3 H CH2CH3
A-1503 CH2OCH2CH2OCH3 CF3 H CH2CH2CH3
A-1504 CH2OCH2CH2OCH3 CF3 H CH2CH2OCH3
A-1505 CH2OCH2CH2OCH3 SO2CH3 CH3 CH3
A-1506 CH2OCH2CH2OCH3 SO2CH3 CH3 CH2CH3
A-1507 CH2OCH2CH2OCH3 SO2CH3 CH3 CH2CH2CH3
A-1508 CH2OCH2CH2OCH3 SO2CH3 CH3 CH2CH2OCH3
A-1509 CH2OCH2CH2OCH3 SO2CH3 CH2CH3 CH3
A-1510 CH2OCH2CH2OCH3 SO2CH3 CH2CH3 CH2CH3
A-151 1 CH2OCH2CH2OCH3 SO2CH3 CH2CH3 CH2CH2CH3
A-1512 CH2OCH2CH2OCH3 SO2CH3 CH2CH3 CH2CH2OCH3
A-1513 CH2OCH2CH2OCH3 SO2CH3 CH2OCH3 CH3
A-1514 CH2OCH2CH2OCH3 SO2CH3 CH2OCH3 CH2CH3
A-1515 CH2OCH2CH2OCH3 SO2CH3 CH2OCH3 CH2CH2CH3
A-1516 CH2OCH2CH2OCH3 SO2CH3 CH2OCH3 CH2CH2OCH3
A-1517 CH2OCH2CH2OCH3 SO2CH3 CH2OCH2CH3 CH3
A-1518 CH2OCH2CH2OCH3 SO2CH3 CH2OCH2CH3 CH2CH3
A-1519 CH2OCH2CH2OCH3 SO2CH3 CH2OCH2CH3 CH2CH2CH3
A-1520 CH2OCH2CH2OCH3 SO2CH3 CH2OCH2CH3 CH2CH2OCH3
A-1521 CH2OCH2CH2OCH3 SO2CH3 CH2(CO)OCH3 CH3
A-1522 CH2OCH2CH2OCH3 SO2CH3 CH2(CO)OCH3 CH2CH3
A-1523 CH2OCH2CH2OCH3 SO2CH3 CH2(CO)OCH3 CH2CH2CH3
A-1524 CH2OCH2CH2OCH3 SO2CH3 CH2(CO)OCH3 CH2CH2OCH3
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
Figure imgf000074_0001
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000082_0001
Figure imgf000083_0001
Examples of preferred compounds I.B, where X is CR2, are the individual compounds compiled in Tables 16 to 210 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a par- ticularly preferred embodiment of the substituents in question.
Figure imgf000083_0002
Table 16 Compounds of formula I.B1 (I.B1 -1 .1 - I.B1 -1 .2048) in which R2 is H, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 17Compounds of formula I.B1 (I.B1 -2.1 - II.B1 -2.2048) in which R2 is H, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 18Compounds of formula I.B1 (I.B1 -3.1 - I.B1 -3.2048) in which R2 is H, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 19Compounds of formula I.B1 (I.B1 -4.1 - I.B1 -4.2048) in which R2 is H, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 20Compounds of formula I.B1 (I.B1 -5.1 - I.B1 -5.2048) in which R2 is H, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 21 Compounds of formula I.B1 (I.B1 -6.1 - I.B1 -6.2048) in which R2 is H, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 22Compounds of formula I.B1 (I.B1 -7.1 - I.B1 -7.2048) in which R2 is H, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 23Compounds of formula I.B1 (I.B1 -8.1 - I.B1 -8.2048) in which R2 is H, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 24Compounds of formula I.B1 (I.B1 -9.1 - I.B1 -9.2048) in which R2 is H, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 25Compounds of formula I.B1 (I.B1 -10.1 - I.B1 -10.2048) in which R2 is H, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 26Compounds of formula I.B1 (I.B1 -1 1 .1 - I.B1 -1 1 .2048) in which R2 is H, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 27Compounds of formula I.B1 (I.B1 -12.1 - I.B1 -12.2048) in which R2 is H, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 28Compounds of formula I.B1 (I.B1 -13.1 - I.B1 -13.2048) in which R2 is H, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 29Compounds of formula I.B1 (I.B1 -14.1 - I.B1 -14.2048) in which R2 is H, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 30Compounds of formula I.B1 (I.B1 -15.1 - I.B1 -15.2048) in which R2 is H, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 31 Compounds of formula I.B2 (I.B2-1 .1 - I.B2-1 .2048) in which R2 is methyl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 32Compounds of formula I.B2 (I.B2-2.1 - ll.B2-2.2048) in which R2 is methyl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 33Compounds of formula I.B2 (I.B2-3.1 - I.B2-3.2048) in which R2 is methyl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 34Compounds of formula I.B2 (I.B2-4.1 - I.B2-4.2048) in which R2 is methyl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 35Compounds of formula I.B2 (I.B2-5.1 - I.B2-5.2048) in which R2 is methyl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 36Compounds of formula I.B2 (I.B2-6.1 - I.B2-6.2048) in which R2 is methyl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 37Compounds of formula I.B2 (I.B2-7.1 - I.B2-7.2048) in which R2 is methyl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 38Compounds of formula I.B2 (I.B2-8.1 - I.B2-8.2048) in which R2 is methyl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 39Compounds of formula I.B2 (I.B2-9.1 - I.B2-9.2048) in which R2 is methyl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 40Compounds of formula I.B2 (I.B2-10.1 - I.B2-10.2048) in which R2 is methyl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 41 Compounds of formula I.B2 (I.B2-1 1 .1 - I.B2-1 1 .2048) in which R2 is methyl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 42Compounds of formula I.B2 (I.B2-12.1 - I.B2-12.2048) in which R2 is methyl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 43Compounds of formula I.B2 (I.B2-13.1 - I.B2-13.2048) in which R2 is methyl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 44Compounds of formula I.B2 (I.B2-14.1 - I.B2-14.2048) in which R2 is methyl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 45Compounds of formula I.B2 (I.B2-15.1 - I.B2-15.2048) in which R2 is methyl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 46Compounds of formula I.B3 (I.B3-1 .1 - I.B3-1 .2048) in which R2 is methylthio, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 47Compounds of formula I.B3 (I.B3-2.1 - ll.B3-2.2048) in which R2 is methylthio, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 48Compounds of formula I.B3 (I.B3-3.1 - I.B3-3.2048) in which R2 is methylthio, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 49Compounds of formula I.B3 (I.B3-4.1 - I.B3-4.2048) in which R2 is methylthio, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 50Compounds of formula I.B3 (I.B3-5.1 - I.B3-5.2048) in which R2 is methylthio, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 51 Compounds of formula I.B3 (I.B3-6.1 - I.B3-6.2048) in which R2 is methylthio, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 52Compounds of formula I.B3 (I.B3-7.1 - I.B3-7.2048) in which R2 is methylthio, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 53Compounds of formula I.B3 (I.B3-8.1 - I.B3-8.2048) in which R2 is methylthio, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 54Compounds of formula I.B3 (I.B3-9.1 - I.B3-9.2048) in which R2 is methylthio, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 55Compounds of formula I.B3 (I.B3-10.1 - I.B3-10.2048) in which R2 is methylthio, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 56Compounds of formula I.B3 (I.B3-1 1 .1 - I.B3-1 1 .2048) in which R2 is methylthio, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 57Compounds of formula I.B3 (I.B3-12.1 - I.B3-12.2048) in which R2 is methylthio, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 58Compounds of formula I.B3 (I.B3-13.1 - I.B3-13.2048) in which R2 is methylthio, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 59Compounds of formula I.B3 (I.B3-14.1 - I.B3-14.2048) in which R2 is methylthio, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 60Compounds of formula I.B3 (I.B3-15.1 - I.B3-15.2048) in which R2 is methylthio, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 61 Compounds of formula I.B4 (I.B4-1 .1 - I.B4-1 .2048) in which R2 is ethylthio, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 62Compounds of formula I.B4 (I.B4-2.1 - ll.B4-2.2048) in which R2 is ethylthio, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 63Compounds of formula I.B4 (I.B4-3.1 - I.B4-3.2048) in which R2 is ethylthio, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 64Compounds of formula I.B4 (I.B4-4.1 - I.B4-4.2048) in which R2 is ethylthio, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 65Compounds of formula I.B4 (I.B4-5.1 - I.B4-5.2048) in which R2 is ethylthio, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 66Compounds of formula I.B4 (I.B4-6.1 - I.B4-6.2048) in which R2 is ethylthio, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 67Compounds of formula I.B4 (I.B4-7.1 - I.B4-7.2048) in which R2 is ethylthio, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 68Compounds of formula I.B4 (I.B4-8.1 - I.B4-8.2048) in which R2 is ethylthio, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 69Compounds of formula I.B4 (I.B4-9.1 - I.B4-9.2048) in which R2 is ethylthio, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 70Compounds of formula I.B4 (I.B4-10.1 - I.B4-10.2048) in which R2 is ethylthio, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 71 Compounds of formula I.B4 (I.B4-1 1 .1 - I.B4-1 1 .2048) in which R2 is ethylthio, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 72Compounds of formula I.B4 (I.B4-12.1 - I.B4-12.2048) in which R2 is ethylthio, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 73Compounds of formula I.B4 (I.B4-13.1 - I.B4-13.2048) in which R2 is ethylthio, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 74Compounds of formula I.B4 (I.B4-14.1 - I.B4-14.2048) in which R2 is ethylthio, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 75Compounds of formula I.B4 (I.B4-15.1 - I.B4-15.2048) in which R2 is ethylthio, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 76Compounds of formula I.B5 (I.B5-1 .1 - I.B5-1 .2048) in which R2 is methylsulfonyl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 77Compounds of formula I.B5 (I.B5-2.1 - ll.B5-2.2048) in which R2 is methylsulfonyl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 78Compounds of formula I.B5 (I.B5-3.1 - I.B5-3.2048) in which R2 is methylsulfonyl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 79Compounds of formula I.B5 (I.B5-4.1 - I.B5-4.2048) in which R2 is methylsulfonyl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 80Compounds of formula I.B5 (I.B5-5.1 - I.B5-5.2048) in which R2 is methylsulfonyl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 81 Compounds of formula I.B5 (I.B5-6.1 - I.B5-6.2048) in which R2 is methylsulfonyl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 82Compounds of formula I.B5 (I.B5-7.1 - I.B5-7.2048) in which R2 is methylsulfonyl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 83Compounds of formula I.B5 (I.B5-8.1 - I.B5-8.2048) in which R2 is methylsulfonyl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 84Compounds of formula I.B5 (I.B5-9.1 - I.B5-9.2048) in which R2 is methylsulfonyl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 85Compounds of formula I.B5 (I.B5-10.1 - I.B5-10.2048) in which R2 is methylsulfonyl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 86Compounds of formula I.B5 (I.B5-1 1 .1 - I.B5-1 1 .2048) in which R2 is methylsulfonyl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 87Compounds of formula I.B5 (I.B5-12.1 - I.B5-12.2048) in which R2 is methylsulfonyl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 88Compounds of formula I.B5 (I.B5-13.1 - I.B5-13.2048) in which R2 is methylsulfonyl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 89Compounds of formula I.B5 (I.B5-14.1 - I.B5-14.2048) in which R2 is methylsulfonyl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 90Compounds of formula I.B5 (I.B5-15.1 - I.B5-15.2048) in which R2 is methylsulfonyl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 91 Compounds of formula I.B6 (I.B6-1 .1 - I.B6-1 .2048) in which R2 is ethylsulfonyl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 92Compounds of formula I.B6 (I.B6-2.1 - ll.B6-2.2048) in which R2 is ethylsulfonyl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 93Compounds of formula I.B6 (I.B6-3.1 - I.B6-3.2048) in which R2 is ethylsulfonyl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 94Compounds of formula I.B6 (I.B6-4.1 - I.B6-4.2048) in which R2 is ethylsulfonyl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 95Compounds of formula I.B6 (I.B6-5.1 - I.B6-5.2048) in which R2 is ethylsulfonyl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 96Compounds of formula I.B6 (I.B6-6.1 - I.B6-6.2048) in which R2 is ethylsulfonyl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 97Compounds of formula I.B6 (I.B6-7.1 - I.B6-7.2048) in which R2 is ethylsulfonyl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 98Compounds of formula I.B6 (I.B6-8.1 - I.B6-8.2048) in which R2 is ethylsulfonyl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 99Compounds of formula I.B6 (I.B6-9.1 - I.B6-9.2048) in which R2 is ethylsulfonyl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table l OOCompounds of formula I.B6 (I.B6-10.1 - I.B6-10.2048) in which R2 is ethylsulfonyl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 101 Compounds of formula I.B6 (I.B6-1 1 .1 - I.B6-1 1 .2048) in which R2 is ethylsulfonyl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 102Compounds of formula I.B6 (I.B6-12.1 - I.B6-12.2048) in which R2 is ethylsulfonyl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 103Compounds of formula I.B6 (I.B6-13.1 - I.B6-13.2048) in which R2 is ethylsulfonyl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 104Compounds of formula I.B6 (I.B6-14.1 - I.B6-14.2048) in which R2 is ethylsulfonyl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 105Compounds of formula I.B6 (I.B6-15.1 - I.B6-15.2048) in which R2 is ethylsulfonyl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 106Compounds of formula I.B7 (I.B7-1 .1 - I.B7-1 .2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 107Compounds of formula I.B7 (I.B7-2.1 - ll.B7-2.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 108Compounds of formula I.B7 (I.B7-3.1 - I.B7-3.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 109Compounds of formula I.B7 (I.B7-4.1 - I.B7-4.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table H OCompounds of formula I.B7 (I.B7-5.1 - I.B7-5.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 1 1 Compounds of formula I.B7 (I.B7-6.1 - I.B7-6.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 12Compounds of formula I.B7 (I.B7-7.1 - I.B7-7.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 13Compounds of formula I.B7 (I.B7-8.1 - I.B7-8.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 14Compounds of formula I.B7 (I.B7-9.1 - I.B7-9.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 1 15Compounds of formula I.B7 (I.B7-10.1 - I.B7-10.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 16Compounds of formula I.B7 (I.B7-1 1 .1 - I.B7-1 1 .2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 17Compounds of formula I.B7 (I.B7-12.1 - I.B7-12.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 18Compounds of formula I.B7 (I.B7-13.1 - I.B7-13.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 1 19Compounds of formula I.B7 (I.B7-14.1 - I.B7-14.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 120Compounds of formula I.B7 (I.B7-15.1 - I.B7-15.2048) in which R2 is trifluoromethyl- methoxymethyl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 121 Compounds of formula I.B8 (I.B8-1 .1 - I.B8-1 .2048) in which R2 is isoxazolin-3-yl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 122Compounds of formula I.B8 (I.B8-2.1 - ll.B8-2.2048) in which R2 is isoxazolin-3-yl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 123Compounds of formula I.B8 (I.B8-3.1 - I.B8-3.2048) in which R2 is isoxazolin-3-yl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 124Compounds of formula I.B8 (I.B8-4.1 - I.B8-4.2048) in which R2 is isoxazolin-3-yl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 125Compounds of formula I.B8 (I.B8-5.1 - I.B8-5.2048) in which R2 is isoxazolin-3-yl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 126Compounds of formula I.B8 (I.B8-6.1 - I.B8-6.2048) in which R2 is isoxazolin-3-yl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 127Compounds of formula I.B8 (I.B8-7.1 - I.B8-7.2048) in which R2 is isoxazolin-3-yl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 128Compounds of formula I.B8 (I.B8-8.1 - I.B8-8.2048) in which R2 is isoxazolin-3-yl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 129Compounds of formula I.B8 (I.B8-9.1 - I.B8-9.2048) in which R2 is isoxazolin-3-yl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 130Compounds of formula I.B8 (I.B8-10.1 - I.B8-10.2048) in which R2 is isoxazolin-3-yl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 131 Compounds of formula I.B8 (I.B8-1 1 .1 - I.B8-1 1 .2048) in which R2 is isoxazolin-3-yl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 132Compounds of formula I.B8 (I.B8-12.1 - I.B8-12.2048) in which R2 is isoxazolin-3-yl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 133Compounds of formula I.B8 (I.B8-13.1 - I.B8-13.2048) in which R2 is isoxazolin-3-yl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 134Compounds of formula I.B8 (I.B8-14.1 - I.B8-14.2048) in which R2 is isoxazolin-3-yl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 135Compounds of formula I.B8 (I.B8-15.1 - I.B8-15.2048) in which R2 is isoxazolin-3-yl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 136Compounds of formula I.B9 (I.B9-1 .1 - I.B9-1 .2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 137Compounds of formula I.B9 (I.B9-2.1 - ll.B9-2.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 138Compounds of formula I.B9 (I.B9-3.1 - I.B9-3.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 139Compounds of formula I.B9 (I.B9-4.1 - I.B9-4.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 140Compounds of formula I.B9 (I.B9-5.1 - I.B9-5.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 141 Compounds of formula I.B9 (I.B9-6.1 - I.B9-6.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 142Compounds of formula I.B9 (I.B9-7.1 - I.B9-7.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 143Compounds of formula I.B9 (I.B9-8.1 - I.B9-8.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 144Compounds of formula I.B9 (I.B9-9.1 - I.B9-9.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 145Compounds of formula I.B9 (I.B9-10.1 - I.B9-10.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 146Compounds of formula I.B9 (I.B9-1 1 .1 - I.B9-1 1 .2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 147Compounds of formula I.B9 (I.B9-12.1 - I.B9-12.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 148Compounds of formula I.B9 (I.B9-13.1 - I.B9-13.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 149Compounds of formula I.B9 (I.B9-14.1 - I.B9-14.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 150Compounds of formula I.B9 (I.B9-15.1 - I.B9-15.2048) in which R2 is 5-methyl- isoxazolin-3-yl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 151 Compounds of formula I.B10 (I.B10-1 .1 - I.B10-1.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 152Compounds of formula I.B10 (I.B10-2.1 - II. B10-2.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 153Compounds of formula I.B10 (I.B10-3.1 - I.B10-3.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 154Compounds of formula I.B10 (I.B10-4.1 - I.B10-4.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 155Compounds of formula I.B10 (I.B10-5.1 - I.B10-5.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 156Compounds of formula I.B10 (I.B10-6.1 - I.B10-6.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 157Compounds of formula I.B10 (I.B10-7.1 - I.B10-7.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 158Compounds of formula I.B10 (I.B10-8.1 - I.B10-8.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 159Compounds of formula I.B10 (I.B10-9.1 - I.B10-9.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 160Compounds of formula I.B10 (I.B10-10.1 - I.B10-10.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 161 Compounds of formula I.B10 (I.B10-1 1 .1 - I.B10-1 1 .2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 162Compounds of formula I.B10 (I.B10-12.1 - I.B10-12.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 163Compounds of formula I.B10 (I.B10-13.1 - I.B10-13.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 164Compounds of formula I.B10 (I.B10-14.1 - I.B10-14.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 165Compounds of formula I.B10 (I.B10-15.1 - I.B10-15.2048) in which R2 is 3-methyl- isoxazolin-5-yl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 166Compounds of formula I.B1 1 (I.B1 1 -1 .1 - I.B1 1 -1.2048) in which R2 is isoxazol-3-yl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 167Compounds of formula I.B1 1 (I. B1 1 -2.1 - II. B1 1 -2.2048) in which R2 is isoxazol-3-yl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 168Compounds of formula I.B1 1 (I. B1 1 -3.1 - 1. B1 1 -3.2048) in which R2 is isoxazol-3-yl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 169Compounds of formula I.B1 1 (I. B1 1 -4.1 - 1. B1 1 -4.2048) in which R2 is isoxazol-3-yl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 170Compounds of formula I.B1 1 (I. B1 1 -5.1 - 1. B1 1 -5.2048) in which R2 is isoxazol-3-yl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 171 Compounds of formula I.B1 1 (I. B1 1 -6.1 - 1. B1 1 -6.2048) in which R2 is isoxazol-3-yl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 172Compounds of formula I.B1 1 (I. B1 1 -7.1 - 1. B1 1 -7.2048) in which R2 is isoxazol-3-yl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 173Compounds of formula I.B1 1 (I. B1 1 -8.1 - 1. B1 1 -8.2048) in which R2 is isoxazol-3-yl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 174Compounds of formula I.B1 1 (I. B1 1 -9.1 - 1. B1 1 -9.2048) in which R2 is isoxazol-3-yl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 175Compounds of formula I.B1 1 (I. B1 1 -10.1 - 1. B1 1 -10.2048) in which R2 is isoxazol-3-yl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 176Compounds of formula I.B1 1 (I. B1 1 -1 1 .1 - I.B1 1 -1 1 .2048) in which R2 is isoxazol-3-yl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 177Compounds of formula I.B1 1 (I. B1 1 -12.1 - 1. B1 1 -12.2048) in which R2 is isoxazol-3-yl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 178Compounds of formula I.B1 1 (I. B1 1 -13.1 - 1. B1 1 -13.2048) in which R2 is isoxazol-3-yl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 179Compounds of formula I.B1 1 (I. B1 1 -14.1 - 1. B1 1 -14.2048) in which R2 is isoxazol-3-yl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 180Compounds of formula I.B1 1 (I. B1 1 -15.1 - 1. B1 1 -15.2048) in which R2 is isoxazol-3-yl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 181 Compounds of formula I.B12 (I.B12-1 .1 - I.B12-1.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 182Compounds of formula I.B12 (I.B12-2.1 - ll.B12-2.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound cor- responds in each case to one row of Table A;
Table 183Compounds of formula I.B12 (I.B12-3.1 - I.B12-3.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 184Compounds of formula I.B12 (I.B12-4.1 - I.B12-4.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 185Compounds of formula I.B12 (I.B12-5.1 - I.B12-5.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 186Compounds of formula I.B12 (I.B12-6.1 - I.B12-6.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 187Compounds of formula I.B12 (I.B12-7.1 - I.B12-7.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound cor- responds in each case to one row of Table A;
Table 188Compounds of formula I.B12 (I.B12-8.1 - I.B12-8.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 189Compounds of formula I.B12 (I.B12-9.1 - I.B12-9.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 190Compounds of formula I.B12 (I.B12-10.1 - I.B12-10.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 191 Compounds of formula I.B12 (I.B12-1 1 .1 - I.B12-1 1 .2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 192Compounds of formula I.B12 (I.B12-12.1 - I.B12-12.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 193Compounds of formula I.B12 (I.B12-13.1 - I.B12-13.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 194Compounds of formula I.B12 (I.B12-14.1 - I.B12-14.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 195Compounds of formula I.B12 (I.B12-15.1 - I.B12-15.2048) in which R2 is 5-methyl- isoxazol-3-yl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 196Compounds of formula I.B13 (I.B13-1 .1 - I.B13-1.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is H and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 197Compounds of formula I.B13 (I.B13-2.1 - II. B13-2.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is H and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 198Compounds of formula I.B13 (I.B13-3.1 - I.B13-3.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is H and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 199Compounds of formula I.B13 (I.B13-4.1 - I.B13-4.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is F and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 200Compounds of formula I.B13 (I.B13-5.1 - I.B13-5.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is F and R5 is F and the combination of R1, R3, R6 and R7 for a compound cor- responds in each case to one row of Table A;
Table 201 Compounds of formula I.B13 (I.B13-6.1 - I.B13-6.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is F and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 202Compounds of formula I.B13 (I.B13-7.1 - I.B13-7.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CI and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 203Compounds of formula I.B13 (I.B13-8.1 - I.B13-8.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CI and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 204Compounds of formula I.B13 (I.B13-9.1 - I.B13-9.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CI and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 205Compounds of formula I.B13 (I.B13-10.1 - I.B13-10.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CN and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A; Table 206Compounds of formula I.B13 (I.B13-1 1 .1 - I.B13-1 1 .2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CN and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 207Compounds of formula I.B13 (I.B13-12.1 - I.B13-12.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CN and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 208Compounds of formula I.B13 (I.B13-13.1 - I.B13-13.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CH3 and R5 is H and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 209Compounds of formula I.B13 (I.B13-14.1 - I.B13-14.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CH3 and R5 is F and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
Table 210Compounds of formula I.B13 (I.B13-15.1 - I.B13-15.2048) in which R2 is 3-methyl- isoxazol-5-yl, R4 is CH3 and R5 is CI and the combination of R1, R3, R6 and R7 for a compound corresponds in each case to one row of Table A;
The compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described hereinafter in schemes 1 to 4. The substituents, variables and indices in schemes 1 to 4 are as defined above for formula I, if not otherwise specified.
The compounds of formula I can be prepared analogous to Scheme 1 below.
Scheme 1 :
Figure imgf000098_0001
(HI) (I)
N-R6-4-R7-1 ,2,4-triazol-3-amine compounds of formula III can be reacted with benzoyl derivatives of formula II to afford compounds of formula I. X is a leaving group, such as halogen, in particular CI, an anhydride residue or an activated ester or activated amide residue. Especially in case of X being halogen the reaction is suitably carried out in the presence of a base. Suitable bases are for example carbonates, such as lithium, sodium or potassium carbonates, amines, such as trimethylamine or triethylamine, and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or 2,4,6-trimethylpyridine. Suitable solvents are in particular aprotic sol- vents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1 ,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trime- thylbenzene, pyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1 ,4-dioxane, N,N-dimethyl formamide, N-methyl pyrrolidinone or mixtures thereof. The starting materials are generally re- acted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of -20°C to 100°C and preferably in the range of -5°C to 50°C.
Alternatively, compounds of formula I can also be prepared as shown in Scheme 2. Reaction of N-R6-4-R7-1 ,2,4-triazol-3-amine of formula III with a benzoic acid derivative of formula IV yields compound I. The reaction is preferably carried out in the presence of a suitable activating agent, which converts the carboxylic acid group of compound IV into an activated ester or an activated amide of formula II. For this purpose activating agents known in the art, such as 1 ,1 ',carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1 -ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC), 2,4,6-tripropyl-1 ,3,5,2,4,6-trioxatriphosphorinane- 2,4,6-trioxide (T3P) or 1 -propanephosphonic acid cyclic anhydride (PPAA) can be employed. The activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting compound IV with the activating agent in the presence of compound III, or in a separate step prior to the reaction with compound III. It may be advantageous, especially in cases where DCC, EDC and PPAA are used as activating agent, to include further additives in the activating reaction, such as hydroxybenzotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4,5-trichlorophenol, N-hydroxysuccinimide or 4-Dimethylamino-pyridine (DMAP). It may further be advantageous to prepare the activated ester or amide in the presence of a base, for example a tertiary amine. The activated ester or amide is either in situ or subsequently reacted with the amine of formula III to afford the amide of formula I. The reaction normally takes place in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. di- chloromethane or dichloroethane, ethers, e.g. tetrahydrofuran or 1 ,4-dioxane or carboxamides, e.g. N,N-dimethylformamide, Ν,Ν-dimethylacetamide or N-methylpyrrolidone. The reaction is ordinarily carried out at temperatures in the range from -20°C to +25°C.
Scheme 2:
Figure imgf000099_0001
(I") (IV) (I)
The compounds of formula II and their respective benzoic acid precursors of formula IV can be purchased or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO 9746530, WO 9831676, WO 9831681 , WO 2002/018352, WO 2000/003988, US
2007/0191335, US 6277847.
Furthermore, compounds of formula I, where R6 is not hydrogen, can be obtained by treating N-(4-R7-1 ,2,4-triazol-3-yl)benzamides of formula V with, for example, alkylating agents such as alkyl halides according to Scheme 3.
Scheme 3. Base, R6-X
Figure imgf000100_0001
The 4-R ,2,4-triazol-3-amine of formula III, where R7 is for example alkyl, can be prepared in a two steps manner (scheme 4). The first step consists of alkylating commercially available 5- nitro-1 H-1 ,2,4-Triazole with an alkylating agent such as a alkyl halide or a dialkylsuflate. An example in the literature can be found in Chemistry in Heterocyclic Compounds, 2005, 41 , 994. The second step is the reduction of the nitro group to the amino group. This reaction is done by known catalytic hydrogenation methods (Pd, Pt, Ni and Zn) or by Metal (Iron, Tin) reduction in acetic medium such as acetic acid or HCI. Some Literature references are quoted below:
Synthesis 2003, 2001 ; Tetrahedron Letters 2005, 46, 2469; Tetrahedron Letters 1999, 40, 7855; Advanced Synthesis and Catalysis 2005, 347,217; Journal of the American Chemical Society 1944, 66, 1781 and Tetrahedron Letters 1984, 25, 839.
Scheme 4:
Figure imgf000100_0002
As a rule, the compounds of formula I including their stereoisomers, salts, tautomers and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds of formula I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystalliza- tion or trituration.
The compounds of formula I and their agriculturally suitable salts are useful as herbicides. They are useful as such or as an appropriately formulated composition. The herbicidal compositions comprising the compound I, in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
Depending on the application method in question, the compounds of formula I, in particu- lar the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted plants. Examples of suitable crops are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus caro- ta, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arbo- reum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usi- tatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Mu- sa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
The term "crop plants" also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information). Here, in general, one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.
Accordingly, the term "crop plants" also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, US 5,013,659) or imidazolinones (see, for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as, for example, glypho- sate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors, such as, for ex- ample, glufosinate (see, for example, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, for example, US 5,559,024).
Numerous crop plants, for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (muta- genesis). Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady® (glypho- sate) and Liberty Link® (glufosinate) have been generated with the aid of genetic engineering methods.
Accordingly, the term "crop plants" also includes plants which, with the aid of genetic en- gineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp. Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B. thuringiensis, such as the endotoxins CrylAb, Cry1 Ac, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 , Cry9c, Cry34Ab1 or Cry35Ab1 ; or vegetative insecticidal proteins (VI Ps), for example VI P1 , VI P2, VI P3, or VIP3A; insecticidal proteins of nema- tode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins of animal organisms, for example wasp, spider or scorpion toxins; fungal toxins, for example from Strep- tomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribo- some-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blockers, for example inhibitors of sodium channels or calcium channels; juvenile hormone esterase; receptors of the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the plants, these toxins may also be produced as pre- toxins, hybrid proteins or truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO
2002/015701 ). Further examples of such toxins or genetically modified plants which produce these toxins are disclosed in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP- A 451 878, WO 03/018810 and WO 03/052073. The methods for producing these genetically modified plants are known to the person skilled in the art and disclosed, for example, in the publications mentioned above. Numerous of the toxins mentioned above bestow, upon the plants by which they are produced, tolerance to pests from all taxonomic classes of arthropods, in particular to beetles (Coeleropta), dipterans (Diptera) and butterflies (Lepidoptera) and to nematodes (Nematoda).
Genetically modified plants which produce one or more genes coding for insecticidal toxins are described, for example, in the publications mentioned above, and some of them are commercially available, such as, for example, YieldGard® (corn varieties producing the toxin CrylAb), YieldGard® Plus (corn varieties which produce the toxins CrylAb and Cry3Bb1 ), Star- link® (corn varieties which produce the toxin Cry9c), Herculex® RW (corn varieties which pro- duce the toxins Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties which produce the toxin CrylAc), Bollgard® I (cotton varieties which produce the toxin CrylAc), Bollgard® II (cotton varieties which produce the toxins CrylAc and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin); NewLeaf® (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin CrylAb and the PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see
WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1 ), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1 F and the PAT enzyme).
Accordingly, the term "crop plants" also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).
Accordingly, the term "crop plants" also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
The term "crop plants" also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for ex- ample by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsatu- rated omega 9 fatty acids (for example Nexera® oilseed rape).
The term "crop plants" also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora® potato).
Furthermore, it has been found that the compounds of formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard, there have been found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.
As desiccants, the compounds of formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
Also of economic interest is to facilitate harvesting, which is made possible by
concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the readily controllable defoliation of useful plants, in particular cotton.
Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.
The compounds of formula I, or the herbicidal compositions comprising the compounds of formula I, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed. The use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.
The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.
Examples of auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.
Examples of thickeners (i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion) are
polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).
Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
Bactericides can be added for stabilizing the aqueous herbicidal formulation. Examples of bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol. Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes.
Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1 , and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
Suitable inert auxiliaries are, for example, the following:
mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also
emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard),
phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and
dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of formula I or la, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
The concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
The formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.
The compounds of formula I of the invention can for example be formulated as follows: 1 . Products for dilution with water
A. Water-soluble concentrates
10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.
B. Dispersible concentrates
20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexa- none with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight.
C. Emulsifiable concentrates
15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.
D. Emulsions
25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.
E. Suspensions
In an agitated ball mill, 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.
F. Water-dispersible granules and water-soluble granules 50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an ac- tive compound content of 50% by weight.
G. Water-dispersible powders and water-soluble powders
75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.
H. Gel formulations
In a ball mill, 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or of an organic solvent are ground to give a fine suspension. Dilution with water gives a stable suspension with active com- pound content of 20% by weight.
2. Products to be applied undiluted
I. Dusts
5 parts by weight of active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dusting powder with an active compound content of 5% by weight.
J. Granules (GR, FG, GG, MG)
0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.
K. ULV solutions (UL)
10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted with an active compound content of 10% by weight.
The compounds of formula I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
In a further embodiment, the compounds of formula I or the herbicidal compositions can be applied by treating seed.
The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multi- layer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula I according to the invention or the compositions prepared therefrom. Here, the herbicid- al compositions can be applied diluted or undiluted.
The term seed comprises seed of all types, such as, for example, corns, seeds, fruits, tu- bers, cuttings and similar forms. Here, preferably, the term seed describes corns and seeds.
The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
The rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. To treat the seed, the compounds of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
It may also be advantageous to use the compounds of formula I in combination with saf- eners. Safeners are chemical compounds which prevent or reduce damage to useful plants without substantially affecting the herbicidal action of the compounds of formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cuttings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of formula I can be used simultaneously or in succession.
Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H- 1 ,2,4-triazole-3-carboxylic acids, 1 -phenyl-4,5-dihydro-5-alkyl-1 H-pyrazole-3,5-dicarboxylic ac- ids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha- oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4- (aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5- thiazolecarboxylic acids, phosphorothiolates and O-phenyl N-alkylcarbamates and their agriculturally useful salts and, provided that they have an acid function, their agriculturally useful deriv- atives, such as amides, esters and thioesters.
To broaden the activity spectrum and to obtain synergistic effects, the compounds of the formula I can be mixed and jointly applied with numerous representatives of other herbicidal or growth-regulating groups of active compounds or with safeners. Suitable mixing partners are, for example, 1 ,2,4-thiadiazoles, 1 ,3,4-thiadiazoles, amides, aminophosphoric acid and its deriv- atives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1 ,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofu- ran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6- tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypro- pionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and also phenylpyrazolines and isoxazolines and their derivatives. Moreover, it may be useful to apply the compounds of formula I alone or in combination with other herbicides or else also mixed with further crop protection agents, jointly, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for alleviating nutritional and trace element deficiencies. Other additives such as nonphytotoxic oils and oil concentrates may also be added.
Examples of herbicides which can be used in combination with the N-(1 ,2,4-triazol-3- yl)arylcarboxamide compounds of formula I according to the present invention are:
b1 ) from the group of the lipid biosynthesis inhibitors:
alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cy- cloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, halox- yfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
b2) from the group of the ALS inhibitors:
amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac- sodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulam- methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, ima- zethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac, pyrimi- nobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfome- turon-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfu- ron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfu- ron-methyl and tritosulfuron;
b3) from the group of the photosynthesis inhibitors:
ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenox- im, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat- dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, me- toxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat- dimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, pro- panil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, ter- bumeton, terbuthylazine, terbutryn, thidiazuron and trietazine;
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, bu- tafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfen- trazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)- pyrimidinyl]-4-fluoro-N-[(isopropyl)methylsulfamoyl]benzamide (H-1 ; CAS 372137-35-4), ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3- yl)phenoxy]-2-pyridyloxy]acetate (H-2; CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1 /-/-pyrazole-1 -carboxamide (H-3; CAS 452098-92-9),
N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole-1 - carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5- methyl-1 H-pyrazole-1 -carboxamide (H-5; CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6- fluoro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide (H-6; CAS 45100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1 ,3,5]triazinan-2,4-dione, 1 ,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4- dihydro-2H-benzo[b][1 ,4]oxazin-6-yl)-1 ,3,5-triazinane-2,4-dione, 2-(2,2,7-Trifluoro-3-oxo-4-prop-
2- ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione and 1 - Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin- 6-yl)-1 H-pyrimidine-2,4-dione;
b5) from the group of the bleacher herbicides:
aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, flu- ridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfu- tole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-hydroxy-
3- [[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2- one (H-7; CAS 352010-68-5) and 4-(3-trifluoromethylphenoxy)-2-(4- trifluoromethylphenyl)pyrimidine (H-8; CAS 180608-33-7);
b6) from the group of the EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors:
bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors:
asulam;
b9) from the group of the mitose inhibitors:
amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlor- propham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;
b10) from the group of the VLCFA inhibitors: acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dime- thenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor;
Compounds of the formula 2:
Figure imgf000111_0001
in which the variables have the following meanings:
Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset, which radicals may be substituted by one to three groups Raa; R21,R22,R23,R24 are H, halogen or Ci-C4-alkyl; X is O or NH; N is 0 or 1 .
Compounds of the formula 2 have in particular the following meanings:
Figure imgf000111_0002
where # denotes the bond to the skeleton of the molecule; and
R2 ,R22,R23,R24 are H, CI, F or CH3; R25 is halogen, Ci-C4-alkyl or Ci-C4-haloalkyl; R26 is Ci-C4 alkyl; R27 is halogen, Ci-C4-alkoxy or Ci-C4-haloalkoxy; R28 is H, halogen, Ci-C4-alkyl, Ci-C4- haloalkyl or Ci-C4-haloalkoxy; M is 0, 1 , 2 or 3; X is oxygen; N is 0 or 1.
Preferred
Figure imgf000111_0003
R21 is H; R22,R23 are F; R24 is H or F; X is oxygen; N is 0 or 1 .
Particularly preferred compounds of the formula 2 are:
3-[5-(2,2-difluoroethoxy)-1 -methyl-3-trifluoromethyl-1 H-pyrazol-4-ylmethane- sulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1 ); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3- trifluoromethyl-1 H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-2); 4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H- [1 ,2,3]triazole (2-3); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5- trifluoromethyl-2H-[1 ,2,3]triazole (2-4); 4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2- methyl-5-trifluoromethyl-2H-[1 ,2,3]triazole (2-5); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3- trifluoromethyl-1 H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-6); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H- [1 ,2,3]triazole (2-7); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3-trifluoromethyl-1 H-pyrazol-4- yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-8); 4-[difluoro-(4- fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluorom
[1 ,2,3]triazole (2-9);
b1 1 ) from the group of the cellulose biosynthesis inhibitors:
chlorthiamid, dichlobenil, flupoxam and isoxaben;
b12) from the group of the decoupler herbicides:
dinoseb, dinoterb and DNOC and its salts;
b13) from the group of the auxin herbicides:
2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts such as aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, MCPA- thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4- pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters;
b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;
b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol- methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dime- thipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flam- prop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fos- amine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6- methylphenoxy)-4-pyridazinol (H-10; CAS 499223-49-3) and its salts and esters.
Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfa- mide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furi- lazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1 - oxa-4-azaspiro[4.5]decane (H-1 1 ; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl)-1 ,3-oxazolidine (H-12; R-29148, CAS 52836-31 -4).
The active compounds of groups b1 ) to b15) and the safeners C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names
(http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide
[Herbicides], Georg Thieme Verlag, Stuttgart, 1995. Further herbicidally active compounds are known from WO 96/26202, WO 97/41 1 16, WO 97/41 1 17, WO 97/41 1 18, WO 01/83459 and WO 2008/074991 and from W. Kramer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1 , Wiley VCH, 2007 and the literature quoted therein.
The invention also relates to compositions in the form of a crop protection composition formulated as a 1 -component composition comprising an active compound combination com- prising at least one N-(1 ,2,4-triazol-3-yl)arylcarboxamide compound of the formula I and at least one further active compound, preferably selected from the active compounds of groups b1 to b15, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.
The invention also relates to compositions in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one compound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound selected from the active compounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where addi- tionally both components may also comprise further auxiliaries customary for crop protection compositions.
In binary compositions comprising at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
In binary compositions comprising at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 .
In ternary compositions comprising both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative parts by weight of the components A:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 ; the weight ratio of the components A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 ; and the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 . Preferably, the weight ratio of the components A + B to the component C is 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.
Examples of particularly preferred compositions according to the invention comprising in each case one individualized compound of the formula I and one mixing partner or a mixing partner combination are given in Table B below.
A further aspect of the invention relates to the compositions B-1 to B-1236 listed in Table
B below, where in each case one row of Table B corresponds to a herbicidal composition comprising one of the compounds of formula I individualized in the above description (component 1 ) and the further active compound from groups b1 ) to b15) and/or safener C stated in each case in the row in question (component 2). The active compounds in the compositions described are in each case preferably present in synergistically effective amounts. Table B:
Herbicide(s) B Safener C
B-1 clodinafop-propargyl —
B-2 cycloxydim —
B-3 cyhalofop-butyl —
B-4 fenoxaprop-P-ethyl —
B-5 pinoxaden —
B-6 profoxydim —
B-7 tepraloxydim —
B-8 tralkoxydim —
B-9 esprocarb —
B-10 prosulfocarb —
B-1 1 thiobencarb —
B-12 triallate —
B-13 bensulfuron-methyl —
B-14 bispyribac-sodium —
B-15 cyclosulfamuron —
B-16 flumetsulam —
B-17 flupyrsulfuron-methyl-sodium —
B-18 foramsulfuron —
B-19 imazamox —
B-20 imazapic —
B-21 imazapyr —
B-22 imazaquin —
B-23 imazethapyr —
B-24 imazosulfuron —
B-25 iodosulfuron-methyl-sodium —
B-26 mesosulfuron —
B-27 nicosulfuron —
B-28 penoxsulam —
B-29 propoxycarbazone-sodium —
B-30 pyrazosulfuron-ethyl —
B-31 pyroxsulam —
B-32 rimsulfuron —
B-33 sulfosulfuron —
B-34 thiencarbazone-methyl —
B-35 tritosulfuron —
B-36 2,4-D and its salts and esters —
B-37 aminopyralid and its salts and esters — Herbicide(s) B Safener C
B-38 clopyralid and its salts and esters —
B-39 dicamba and its salts and esters —
B-40 fluroxypyr-meptyl —
B-41 quinclorac —
B-42 quinmerac —
B-43 H-9 —
B-44 diflufenzopyr —
B-45 diflufenzopyr-sodium —
B-46 clomazone —
B-47 diflufenican —
B-48 fluorochloridone —
B-49 isoxaflutol —
B-50 mesotrione —
B-51 picolinafen —
B-52 sulcotrione —
B-53 tefuryltrione —
B-54 tembotrione —
B-55 topramezone —
B-56 H-7 —
B-57 atrazine —
B-58 diuron —
B-59 fluometuron —
B-60 hexazinone —
B-61 isoproturon —
B-62 metribuzin —
B-63 propanil —
B-64 terbuthylazine —
B-65 paraquat dichloride —
B-66 flumioxazin —
B-67 oxyfluorfen —
B-68 saflufenacil —
B-69 sulfentrazone —
B-70 H-1 —
B-71 H-2 —
B-72 glyphosate —
B-73 glyphosate-isopropylammonium —
B-74 glyphosate-trimesium (sulfosate) —
B-75 glufosinate —
B-76 glufosinate-ammonium — Herbicide(s) B Safener C
B-77 pendimethalin —
B-78 trifluralin —
B-79 acetochlor —
B-80 cafenstrole —
B-81 dimethenamid-P —
B-82 fentrazamide —
B-83 flufenacet —
B-84 mefenacet —
B-85 metazachlor —
B-86 metolachlor-S —
B-87 pyroxasulfone —
B-88 isoxaben —
B-89 dymron —
B-90 indanofan —
B-91 oxaziclomefone —
B-92 triaziflam —
B-93 chlorotoluron —
B-94 atrazine + H-1 —
B-95 atrazine + glyphosate —
B-96 atrazine + mesotrione —
B-97 atrazine + nicosulfuron —
B-98 atrazine + tembotrione —
B-99 atrazine + topramezone —
B-100 clomazone + glyphosate —
B-101 diflufenican + clodinafop-propargyl —
B-102 diflufenican + fenoxaprop-P-ethyl —
B-103 diflufenican + flupyrsulfuron-methyl-sodium —
B-104 diflufenican + glyphosate —
B-105 diflufenican + mesosulfuron-methyl —
B-106 diflufenican + pinoxaden —
B-107 diflufenican + pyroxsulam —
B-108 flumetsulam + glyphosate —
B-109 flumioxazin + glyphosate —
B-1 10 imazapic + glyphosate —
B-1 1 1 imazethapyr + glyphosate —
B-1 12 isoxaflutol + H-1 —
B-1 13 isoxaflutol + glyphosate —
B-1 14 metazachlor + H-1 —
B-1 15 metazachlor + glyphosate — Herbicide(s) B Safener C
B-1 16 metazachlor + mesotrione —
B-1 17 metazachlor + nicosulfuron —
B-1 18 metazachlor + terbuthylazine —
B-1 19 metazachlor + topramezone —
B-120 metribuzin + glyphosate —
B-121 pendimethalin + H-1 —
B-122 pendimethalin + clodinafop-propargyl —
B-123 pendimethalin + fenoxaprop-P-ethyl —
B-124 pendimethalin + flupyrsulfuron-methyl-sodium —
B-125 pendimethalin + glyphosate —
B-126 pendimethalin + mesosulfuron-methyl —
B-127 pendimethalin + mesotrione —
B-128 pendimethalin + nicosulfuron —
B-129 pendimethalin + pinoxaden —
B-130 pendimethalin + pyroxsulam —
B-131 pendimethalin + tembotrione —
B-132 pendimethalin + topramezone —
B-133 pyroxasulfone + tembotrione —
B-134 pyroxasulfone + topramezone —
B-135 sulfentrazone + glyphosate —
B-136 terbuthylazine + H-1 —
B-137 terbuthylazine + foramsulfuron —
B-138 terbuthylazine + glyphosate —
B-139 terbuthylazine + mesotrione —
B-140 terbuthylazine + nicosulfuron —
B-141 terbuthylazine + tembotrione —
B-142 terbuthylazine + topramezone —
B-143 trifluralin + glyphosate —
B-144 — benoxacor
B-145 — cloquintocet
B-146 — cyprosulfamide
B-147 — dichlormid
B-148 — fenchlorazole
B-149 — isoxadifen
B-150 — mefenpyr
B-151 — H-1 1
B-152 — H-12
B-153 clodinafop-propargyl benoxacor
B-154 cycloxydim benoxacor Herbicide(s) B Safener C
B-155 cyhalofop-butyl benoxacor
B-156 fenoxaprop-P-ethyl benoxacor
B-157 pinoxaden benoxacor
B-158 profoxydim benoxacor
B-159 tepraloxydim benoxacor
B-160 tralkoxydim benoxacor
B-161 esprocarb benoxacor
B-162 prosulfocarb benoxacor
B-163 thiobencarb benoxacor
B-164 triallate benoxacor
B-165 bensulfuron-methyl benoxacor
B-166 bispyribac-sodium benoxacor
B-167 cyclosulfamuron benoxacor
B-168 flumetsulam benoxacor
B-169 flupyrsulfuron-methyl-sodium benoxacor
B-170 foramsulfuron benoxacor
B-171 imazamox benoxacor
B-172 imazapic benoxacor
B-173 imazapyr benoxacor
B-174 imazaquin benoxacor
B-175 imazethapyr benoxacor
B-176 imazosulfuron benoxacor
B-177 iodosulfuron-methyl-sodium benoxacor
B-178 mesosulfuron benoxacor
B-179 nicosulfuron benoxacor
B-180 penoxsulam benoxacor
B-181 propoxycarbazone-sodium benoxacor
B-182 pyrazosulfuron-ethyl benoxacor
B-183 pyroxsulam benoxacor
B-184 rimsulfuron benoxacor
B-185 sulfosulfuron benoxacor
B-186 thiencarbazone-methyl benoxacor
B-187 tritosulfuron benoxacor
B-188 2,4-D and its salts and esters benoxacor
B-189 aminopyralid and its salts and esters benoxacor
B-190 clopyralid and its salts and esters benoxacor
B-191 dicamba and its salts and esters benoxacor
B-192 fluroxypyr-meptyl benoxacor
B-193 quinclorac benoxacor Herbicide(s) B Safener C
B-194 quinmerac benoxacor
B-195 H-9 benoxacor
B-196 diflufenzopyr benoxacor
B-197 diflufenzopyr-sodium benoxacor
B-198 clomazone benoxacor
B-199 diflufenican benoxacor
B-200 fluorochloridone benoxacor
B-201 isoxaflutol benoxacor
B-202 mesotrione benoxacor
B-203 picolinafen benoxacor
B-204 sulcotrione benoxacor
B-205 tefuryltrione benoxacor
B-206 tembotrione benoxacor
B-207 topramezone benoxacor
B-208 H-7 benoxacor
B-209 atrazine benoxacor
B-210 diuron benoxacor
B-21 1 fluometuron benoxacor
B-212 hexazinone benoxacor
B-213 isoproturon benoxacor
B-214 metribuzin benoxacor
B-215 propanil benoxacor
B-216 terbuthylazine benoxacor
B-217 paraquat dichloride benoxacor
B-218 flumioxazin benoxacor
B-219 oxyfluorfen benoxacor
B-220 saflufenacil benoxacor
B-221 sulfentrazone benoxacor
B-222 H-1 benoxacor
B-223 H-2 benoxacor
B-224 glyphosate benoxacor
B-225 glyphosate-isopropylammonium benoxacor
B-226 glyphosate-trimesium (sulfosate) benoxacor
B-227 glufosinate benoxacor
B-228 glufosinate-ammonium benoxacor
B-229 pendimethalin benoxacor
B-230 trifluralin benoxacor
B-231 acetochlor benoxacor
B-232 cafenstrole benoxacor Herbicide(s) B Safener C
B-233 dimethenamid-P benoxacor
B-234 fentrazamide benoxacor
B-235 flufenacet benoxacor
B-236 mefenacet benoxacor
B-237 metazachlor benoxacor
B-238 metolachlor-S benoxacor
B-239 pyroxasulfone benoxacor
B-240 isoxaben benoxacor
B-241 dymron benoxacor
B-242 indanofan benoxacor
B-243 oxaziclomefone benoxacor
B-244 triaziflam benoxacor
B-245 atrazine + H-1 benoxacor
B-246 atrazine + glyphosate benoxacor
B-247 atrazine + mesotrione benoxacor
B-248 atrazine + nicosulfuron benoxacor
B-249 atrazine + tembotrione benoxacor
B-250 atrazine + topramezone benoxacor
B-251 clomazone + glyphosate benoxacor
B-252 diflufenican + clodinafop-propargyl benoxacor
B-253 diflufenican + fenoxaprop-P-ethyl benoxacor
B-254 diflufenican + flupyrsulfuron-methyl-sodium benoxacor
B-255 diflufenican + glyphosate benoxacor
B-256 diflufenican + mesosulfuron-methyl benoxacor
B-257 diflufenican + pinoxaden benoxacor
B-258 diflufenican + pyroxsulam benoxacor
B-259 flumetsulam + glyphosate benoxacor
B-260 flumioxazin + glyphosate benoxacor
B-261 imazapic + glyphosate benoxacor
B-262 imazethapyr + glyphosate benoxacor
B-263 isoxaflutol + H-1 benoxacor
B-264 isoxaflutol + glyphosate benoxacor
B-265 metazachlor + H-1 benoxacor
B-266 metazachlor + glyphosate benoxacor
B-267 metazachlor + mesotrione benoxacor
B-268 metazachlor + nicosulfuron benoxacor
B-269 metazachlor + terbuthylazine benoxacor
B-270 metazachlor + topramezone benoxacor
B-271 metribuzin + glyphosate benoxacor Herbicide(s) B Safener C
B-272 pendimethalin + H-1 benoxacor
B-273 pendimethalin + clodinafop-propargyl benoxacor
B-274 pendimethalin + fenoxaprop-P-ethyl benoxacor
B-275 pendimethalin + flupyrsulfuron-methyl-sodium benoxacor
B-276 pendimethalin + glyphosate benoxacor
B-277 pendimethalin + mesosulfuron-methyl benoxacor
B-278 pendimethalin + mesotrione benoxacor
B-279 pendimethalin + nicosulfuron benoxacor
B-280 pendimethalin + pinoxaden benoxacor
B-281 pendimethalin + pyroxsulam benoxacor
B-282 pendimethalin + tembotrione benoxacor
B-283 pendimethalin + topramezone benoxacor
B-284 pyroxasulfone + tembotrione benoxacor
B-285 pyroxasulfone + topramezone benoxacor
B-286 sulfentrazone + glyphosate benoxacor
B-287 terbuthylazine + H-1 benoxacor
B-288 terbuthylazine + foramsulfuron benoxacor
B-289 terbuthylazine + glyphosate benoxacor
B-290 terbuthylazine + mesotrione benoxacor
B-291 terbuthylazine + nicosulfuron benoxacor
B-292 terbuthylazine + tembotrione benoxacor
B-293 terbuthylazine + topramezone benoxacor
B-294 trifluralin + glyphosate benoxacor
B-295 clodinafop-propargyl cloquintocet
B-296 cycloxydim cloquintocet
B-297 cyhalofop-butyl cloquintocet
B-298 fenoxaprop-P-ethyl cloquintocet
B-299 pinoxaden cloquintocet
B-300 profoxydim cloquintocet
B-301 tepraloxydim cloquintocet
B-302 tralkoxydim cloquintocet
B-303 esprocarb cloquintocet
B-304 prosulfocarb cloquintocet
B-305 thiobencarb cloquintocet
B-306 triallate cloquintocet
B-307 bensulfuron-methyl cloquintocet
B-308 bispyribac-sodium cloquintocet
B-309 cyclosulfamuron cloquintocet
B-310 flumetsulam cloquintocet Herbicide(s) B Safener C
B-31 1 flupyrsulfuron-methyl-sodium cloquintocet
B-312 foramsulfuron cloquintocet
B-313 imazamox cloquintocet
B-314 imazapic cloquintocet
B-315 imazapyr cloquintocet
B-316 imazaquin cloquintocet
B-317 imazethapyr cloquintocet
B-318 imazosulfuron cloquintocet
B-319 iodosulfuron-methyl-sodium cloquintocet
B-320 mesosulfuron cloquintocet
B-321 nicosulfuron cloquintocet
B-322 penoxsulam cloquintocet
B-323 propoxycarbazone-sodium cloquintocet
B-324 pyrazosulfuron-ethyl cloquintocet
B-325 pyroxsulam cloquintocet
B-326 rimsulfuron cloquintocet
B-327 sulfosulfuron cloquintocet
B-328 thiencarbazone-methyl cloquintocet
B-329 tritosulfuron cloquintocet
B-330 2,4-D and its salts and esters cloquintocet
B-331 aminopyralid and its salts and esters cloquintocet
B-332 clopyralid and its salts and esters cloquintocet
B-333 dicamba and its salts and esters cloquintocet
B-334 fluroxypyr-meptyl cloquintocet
B-335 quinclorac cloquintocet
B-336 quinmerac cloquintocet
B-337 H-9 cloquintocet
B-338 diflufenzopyr cloquintocet
B-339 diflufenzopyr-sodium cloquintocet
B-340 clomazone cloquintocet
B-341 diflufenican cloquintocet
B-342 fluorochloridone cloquintocet
B-343 isoxaflutol cloquintocet
B-344 mesotrione cloquintocet
B-345 picolinafen cloquintocet
B-346 sulcotrione cloquintocet
B-347 tefuryltrione cloquintocet
B-348 tembotrione cloquintocet
B-349 topramezone cloquintocet Herbicide(s) B Safener C
B-350 H-7 cloquintocet
B-351 atrazine cloquintocet
B-352 diuron cloquintocet
B-353 fluometuron cloquintocet
B-354 hexazinone cloquintocet
B-355 isoproturon cloquintocet
B-356 metribuzin cloquintocet
B-357 propanil cloquintocet
B-358 terbuthylazine cloquintocet
B-359 paraquat dichloride cloquintocet
B-360 flumioxazin cloquintocet
B-361 oxyfluorfen cloquintocet
B-362 saflufenacil cloquintocet
B-363 sulfentrazone cloquintocet
B-364 H-1 cloquintocet
B-365 H-2 cloquintocet
B-366 glyphosate cloquintocet
B-367 glyphosate-isopropylammonium cloquintocet
B-368 glyphosate-trimesium (sulfosate) cloquintocet
B-369 glufosinate cloquintocet
B-370 glufosinate-ammonium cloquintocet
B-371 pendimethalin cloquintocet
B-372 trifluralin cloquintocet
B-373 acetochlor cloquintocet
B-374 cafenstrole cloquintocet
B-375 dimethenamid-P cloquintocet
B-376 fentrazamide cloquintocet
B-377 flufenacet cloquintocet
B-378 mefenacet cloquintocet
B-379 metazachlor cloquintocet
B-380 metolachlor-S cloquintocet
B-381 pyroxasulfone cloquintocet
B-382 isoxaben cloquintocet
B-383 dymron cloquintocet
B-384 indanofan cloquintocet
B-385 oxaziclomefone cloquintocet
B-386 triaziflam cloquintocet
B-387 atrazine + H-1 cloquintocet
B-388 atrazine + glyphosate cloquintocet Herbicide(s) B Safener C
B-389 atrazine + mesotrione cloquintocet
B-390 atrazine + nicosulfuron cloquintocet
B-391 atrazine + tembotrione cloquintocet
B-392 atrazine + topramezone cloquintocet
B-393 clomazone + glyphosate cloquintocet
B-394 diflufenican + clodinafop-propargyl cloquintocet
B-395 diflufenican + fenoxaprop-p-ethyl cloquintocet
B-396 diflufenican + flupyrsulfuron-methyl-sodium cloquintocet
B-397 diflufenican + glyphosate cloquintocet
B-398 diflufenican + mesosulfuron-methyl cloquintocet
B-399 diflufenican + pinoxaden cloquintocet
B-400 diflufenican + pyroxsulam cloquintocet
B-401 flumetsulam + glyphosate cloquintocet
B-402 flumioxazin + glyphosate cloquintocet
B-403 imazapic + glyphosate cloquintocet
B-404 imazethapyr + glyphosate cloquintocet
B-405 isoxaflutol + H-1 cloquintocet
B-406 isoxaflutol + glyphosate cloquintocet
B-407 metazachlor + H-1 cloquintocet
B-408 metazachlor + glyphosate cloquintocet
B-409 metazachlor + mesotrione cloquintocet
B-410 metazachlor + nicosulfuron cloquintocet
B-41 1 metazachlor + terbuthylazine cloquintocet
B-412 metazachlor + topramezone cloquintocet
B-413 metribuzin + glyphosate cloquintocet
B-414 pendimethalin + H-1 cloquintocet
B-415 pendimethalin + clodinafop-propargyl cloquintocet
B-416 pendimethalin + fenoxaprop-P-ethyl cloquintocet
B-417 pendimethalin + flupyrsulfuron-methyl-sodium cloquintocet
B-418 pendimethalin + glyphosate cloquintocet
B-419 pendimethalin + mesosulfuron-methyl cloquintocet
B-420 pendimethalin + mesotrione cloquintocet
B-421 pendimethalin + nicosulfuron cloquintocet
B-422 pendimethalin + pinoxaden cloquintocet
B-423 pendimethalin + pyroxsulam cloquintocet
B-424 pendimethalin + tembotrione cloquintocet
B-425 pendimethalin + topramezone cloquintocet
B-426 pyroxasulfone + tembotrione cloquintocet
B-427 pyroxasulfone + topramezone cloquintocet Herbicide(s) B Safener C
B-428 sulfentrazone + glyphosate cloquintocet
B-429 terbuthylazine + H-1 cloquintocet
B-430 terbuthylazine + foramsulfuron cloquintocet
B-431 terbuthylazine + glyphosate cloquintocet
B-432 terbuthylazine + mesotrione cloquintocet
B-433 terbuthylazine + nicosulfuron cloquintocet
B-434 terbuthylazine + tembotrione cloquintocet
B-435 terbuthylazine + topramezone cloquintocet
B-436 trifluralin + glyphosate cloquintocet
B-437 clodinafop-propargyl dichlormid
B-438 cycloxydim dichlormid
B-439 cyhalofop-butyl dichlormid
B-440 fenoxaprop-P-ethyl dichlormid
B-441 pinoxaden dichlormid
B-442 profoxydim dichlormid
B-443 tepraloxydim dichlormid
B-444 tralkoxydim dichlormid
B-445 esprocarb dichlormid
B-446 prosulfocarb dichlormid
B-447 thiobencarb dichlormid
B-448 triallate dichlormid
B-449 bensulfuron-methyl dichlormid
B-450 bispyribac-sodium dichlormid
B-451 cyclosulfamuron dichlormid
B-452 flumetsulam dichlormid
B-453 flupyrsulfuron-methyl-sodium dichlormid
B-454 foramsulfuron dichlormid
B-455 imazamox dichlormid
B-456 imazapic dichlormid
B-457 imazapyr dichlormid
B-458 imazaquin dichlormid
B-459 imazethapyr dichlormid
B-460 imazosulfuron dichlormid
B-461 iodosulfuron-methyl-sodium dichlormid
B-462 mesosulfuron dichlormid
B-463 nicosulfuron dichlormid
B-464 penoxsulam dichlormid
B-465 propoxycarbazone-sodium dichlormid
B-466 pyrazosulfuron-ethyl dichlormid Herbicide(s) B Safener C
B-467 pyroxsulam dichlormid
B-468 rimsulfuron dichlormid
B-469 sulfosulfuron dichlormid
B-470 thiencarbazone-methyl dichlormid
B-471 tritosulfuron dichlormid
B-472 2,4-D and its salts and esters dichlormid
B-473 aminopyralid and its salts and esters dichlormid
B-474 clopyralid and its salts and esters dichlormid
B-475 dicamba and its salts and esters dichlormid
B-476 fluroxypyr-meptyl dichlormid
B-477 quinclorac dichlormid
B-478 quinmerac dichlormid
B-479 H-9 dichlormid
B-480 diflufenzopyr dichlormid
B-481 diflufenzopyr-sodium dichlormid
B-482 clomazone dichlormid
B-483 diflufenican dichlormid
B-484 fluorochloridone dichlormid
B-485 isoxaflutol dichlormid
B-486 mesotrione dichlormid
B-487 picolinafen dichlormid
B-488 sulcotrione dichlormid
B-489 tefuryltrione dichlormid
B-490 tembotrione dichlormid
B-491 topramezone dichlormid
B-492 H-7 dichlormid
B-493 atrazine dichlormid
B-494 diuron dichlormid
B-495 fluometuron dichlormid
B-496 hexazinone dichlormid
B-497 isoproturon dichlormid
B-498 metribuzin dichlormid
B-499 propanil dichlormid
B-500 terbuthylazine dichlormid
B-501 paraquat dichloride dichlormid
B-502 flumioxazin dichlormid
B-503 oxyfluorfen dichlormid
B-504 saflufenacil dichlormid
B-505 sulfentrazone dichlormid Herbicide(s) B Safener C
B-506 H-1 dichlormid
B-507 H-2 dichlormid
B-508 glyphosate dichlormid
B-509 glyphosate-isopropylammonium dichlormid
B-510 glyphosate-trimesium (sulfosate) dichlormid
B-51 1 glufosinate dichlormid
B-512 glufosinate-ammonium dichlormid
B-513 pendimethalin dichlormid
B-514 trifluralin dichlormid
B-515 acetochlor dichlormid
B-516 cafenstrole dichlormid
B-517 dimethenamid-P dichlormid
B-518 fentrazamide dichlormid
B-519 flufenacet dichlormid
B-520 mefenacet dichlormid
B-521 metazachlor dichlormid
B-522 metolachlor-S dichlormid
B-523 pyroxasulfone dichlormid
B-524 isoxaben dichlormid
B-525 dymron dichlormid
B-526 indanofan dichlormid
B-527 oxaziclomefone dichlormid
B-528 triaziflam dichlormid
B-529 atrazine + H-1 dichlormid
B-530 atrazine + glyphosate dichlormid
B-531 atrazine + mesotrione dichlormid
B-532 atrazine + nicosulfuron dichlormid
B-533 atrazine + tembotrione dichlormid
B-534 atrazine + topramezone dichlormid
B-535 clomazone + glyphosate dichlormid
B-536 diflufenican + clodinafop-propargyl dichlormid
B-537 diflufenican + fenoxaprop-p-ethyl dichlormid
B-538 diflufenican + flupyrsulfuron-methyl-sodium dichlormid
B-539 diflufenican + glyphosate dichlormid
B-540 diflufenican + mesosulfuron-methyl dichlormid
B-541 diflufenican + pinoxaden dichlormid
B-542 diflufenican + pyroxsulam dichlormid
B-543 flumetsulam + glyphosate dichlormid
B-544 flumioxazin + glyphosate dichlormid Herbicide(s) B Safener C
B-545 imazapic + glyphosate dichlormid
B-546 imazethapyr + glyphosate dichlormid
B-547 isoxaflutol + H-1 dichlormid
B-548 isoxaflutol + glyphosate dichlormid
B-549 metazachlor + H-1 dichlormid
B-550 metazachlor + glyphosate dichlormid
B-551 metazachlor + mesotrione dichlormid
B-552 metazachlor + nicosulfuron dichlormid
B-553 metazachlor + terbuthylazine dichlormid
B-554 metazachlor + topramezone dichlormid
B-555 metribuzin + glyphosate dichlormid
B-556 pendimethalin + H-1 dichlormid
B-557 pendimethalin + clodinafop-propargyl dichlormid
B-558 pendimethalin + fenoxaprop-P-ethyl dichlormid
B-559 pendimethalin + flupyrsulfuron-methyl-sodium dichlormid
B-560 pendimethalin + glyphosate dichlormid
B-561 pendimethalin + mesosulfuron-methyl dichlormid
B-562 pendimethalin + mesotrione dichlormid
B-563 pendimethalin + nicosulfuron dichlormid
B-564 pendimethalin + pinoxaden dichlormid
B-565 pendimethalin + pyroxsulam dichlormid
B-566 pendimethalin + tembotrione dichlormid
B-567 pendimethalin + topramezone dichlormid
B-568 pyroxasulfone + tembotrione dichlormid
B-569 pyroxasulfone + topramezone dichlormid
B-570 sulfentrazone + glyphosate dichlormid
B-571 terbuthylazine + H-1 dichlormid
B-572 terbuthylazine + foramsulfuron dichlormid
B-573 terbuthylazine + glyphosate dichlormid
B-574 terbuthylazine + mesotrione dichlormid
B-575 terbuthylazine + nicosulfuron dichlormid
B-576 terbuthylazine + tembotrione dichlormid
B-577 terbuthylazine + topramezone dichlormid
B-578 trifluralin + glyphosate dichlormid
B-579 clodinafop-propargyl fenchlorazole
B-580 cycloxydim fenchlorazole
B-581 cyhalofop-butyl fenchlorazole
B-582 fenoxaprop-P-ethyl fenchlorazole
B-583 pinoxaden fenchlorazole Herbicide(s) B Safener C
B-584 profoxydim fenchlorazole
B-585 tepraloxydim fenchlorazole
B-586 tralkoxydim fenchlorazole
B-587 esprocarb fenchlorazole
B-588 prosulfocarb fenchlorazole
B-589 thiobencarb fenchlorazole
B-590 triallate fenchlorazole
B-591 bensulfuron-methyl fenchlorazole
B-592 bispyribac-sodium fenchlorazole
B-593 cyclosulfamuron fenchlorazole
B-594 flumetsulam fenchlorazole
B-595 flupyrsulfuron-methyl-sodium fenchlorazole
B-596 foramsulfuron fenchlorazole
B-597 imazamox fenchlorazole
B-598 imazapic fenchlorazole
B-599 imazapyr fenchlorazole
B-600 imazaquin fenchlorazole
B-601 imazethapyr fenchlorazole
B-602 imazosulfuron fenchlorazole
B-603 iodosulfuron-methyl-sodium fenchlorazole
B-604 mesosulfuron fenchlorazole
B-605 nicosulfuron fenchlorazole
B-606 penoxsulam fenchlorazole
B-607 propoxycarbazone-sodium fenchlorazole
B-608 pyrazosulfuron-ethyl fenchlorazole
B-609 pyroxsulam fenchlorazole
B-610 rimsulfuron fenchlorazole
B-61 1 sulfosulfuron fenchlorazole
B-612 thiencarbazone-methyl fenchlorazole
B-613 tritosulfuron fenchlorazole
B-614 2,4-D and its salts and esters fenchlorazole
B-615 aminopyralid and its salts and esters fenchlorazole
B-616 clopyralid and its salts and esters fenchlorazole
B-617 dicamba and its salts and esters fenchlorazole
B-618 fluroxypyr-meptyl fenchlorazole
B-619 quinclorac fenchlorazole
B-620 quinmerac fenchlorazole
B-621 H-9 fenchlorazole
B-622 diflufenzopyr fenchlorazole Herbicide(s) B Safener C
B-623 diflufenzopyr-sodium fenchlorazole
B-624 clomazone fenchlorazole
B-625 diflufenican fenchlorazole
B-626 fluorochloridone fenchlorazole
B-627 isoxaflutol fenchlorazole
B-628 mesotrione fenchlorazole
B-629 picolinafen fenchlorazole
B-630 sulcotrione fenchlorazole
B-631 tefuryltrione fenchlorazole
B-632 tembotrione fenchlorazole
B-633 topramezone fenchlorazole
B-634 H-7 fenchlorazole
B-635 atrazine fenchlorazole
B-636 diuron fenchlorazole
B-637 fluometuron fenchlorazole
B-638 hexazinone fenchlorazole
B-639 isoproturon fenchlorazole
B-640 metribuzin fenchlorazole
B-641 propanil fenchlorazole
B-642 terbuthylazine fenchlorazole
B-643 paraquat dichloride fenchlorazole
B-644 flumioxazin fenchlorazole
B-645 oxyfluorfen fenchlorazole
B-646 saflufenacil fenchlorazole
B-647 sulfentrazone fenchlorazole
B-648 H-1 fenchlorazole
B-649 H-2 fenchlorazole
B-650 glyphosate fenchlorazole
B-651 glyphosate-isopropylammonium fenchlorazole
B-652 glyphosate-trimesium (sulfosate) fenchlorazole
B-653 glufosinate fenchlorazole
B-654 glufosinate-ammonium fenchlorazole
B-655 pendimethalin fenchlorazole
B-656 trifluralin fenchlorazole
B-657 acetochlor fenchlorazole
B-658 cafenstrole fenchlorazole
B-659 dimethenamid-P fenchlorazole
B-660 fentrazamide fenchlorazole
B-661 flufenacet fenchlorazole Herbicide(s) B Safener C
B-662 mefenacet fenchlorazole
B-663 metazachlor fenchlorazole
B-664 metolachlor-S fenchlorazole
B-665 pyroxasulfone fenchlorazole
B-666 isoxaben fenchlorazole
B-667 dymron fenchlorazole
B-668 indanofan fenchlorazole
B-669 oxaziclomefone fenchlorazole
B-670 triaziflam fenchlorazole
B-671 atrazine + H-1 fenchlorazole
B-672 atrazine + glyphosate fenchlorazole
B-673 atrazine + mesotrione fenchlorazole
B-674 atrazine + nicosulfuron fenchlorazole
B-675 atrazine + tembotrione fenchlorazole
B-676 atrazine + topramezone fenchlorazole
B-677 clomazone + glyphosate fenchlorazole
B-678 diflufenican + clodinafop-propargyl fenchlorazole
B-679 diflufenican + fenoxaprop-P-ethyl fenchlorazole
B-680 diflufenican + flupyrsulfuron-methyl-sodium fenchlorazole
B-681 diflufenican + glyphosate fenchlorazole
B-682 diflufenican + mesosulfuron-methyl fenchlorazole
B-683 diflufenican + pinoxaden fenchlorazole
B-684 diflufenican + pyroxsulam fenchlorazole
B-685 flumetsulam + glyphosate fenchlorazole
B-686 flumioxazin + glyphosate fenchlorazole
B-687 imazapic + glyphosate fenchlorazole
B-688 imazethapyr + glyphosate fenchlorazole
B-689 isoxaflutol + H-1 fenchlorazole
B-690 isoxaflutol + glyphosate fenchlorazole
B-691 metazachlor + H-1 fenchlorazole
B-692 metazachlor + glyphosate fenchlorazole
B-693 metazachlor + mesotrione fenchlorazole
B-694 metazachlor + nicosulfuron fenchlorazole
B-695 metazachlor + terbuthylazine fenchlorazole
B-696 metazachlor + topramezone fenchlorazole
B-697 metribuzin + glyphosate fenchlorazole
B-698 pendimethalin + H-1 fenchlorazole
B-699 pendimethalin + clodinafop-propargyl fenchlorazole
B-700 pendimethalin + fenoxaprop-P-ethyl fenchlorazole Herbicide(s) B Safener C
B-701 pendimethalin + flupyrsulfuron-methyl-sodium fenchlorazole
B-702 pendimethalin + glyphosate fenchlorazole
B-703 pendimethalin + mesosulfuron-methyl fenchlorazole
B-704 pendimethalin + mesotrione fenchlorazole
B-705 pendimethalin + nicosulfuron fenchlorazole
B-706 pendimethalin + pinoxaden fenchlorazole
B-707 pendimethalin + pyroxsulam fenchlorazole
B-708 pendimethalin + tembotrione fenchlorazole
B-709 pendimethalin + topramezone fenchlorazole
B-710 pyroxasulfone + tembotrione fenchlorazole
B-71 1 pyroxasulfone + topramezone fenchlorazole
B-712 sulfentrazone + glyphosate fenchlorazole
B-713 terbuthylazine + H-1 fenchlorazole
B-714 terbuthylazine + foramsulfuron fenchlorazole
B-715 terbuthylazine + glyphosate fenchlorazole
B-716 terbuthylazine + mesotrione fenchlorazole
B-717 terbuthylazine + nicosulfuron fenchlorazole
B-718 terbuthylazine + tembotrione fenchlorazole
B-719 terbuthylazine + topramezone fenchlorazole
B-720 trifluralin + glyphosate fenchlorazole
B-721 clodinafop-propargyl isoxadifen
B-722 cycloxydim isoxadifen
B-723 cyhalofop-butyl isoxadifen
B-724 fenoxaprop-P-ethyl isoxadifen
B-725 pinoxaden isoxadifen
B-726 profoxydim isoxadifen
B-727 tepraloxydim isoxadifen
B-728 tralkoxydim isoxadifen
B-729 esprocarb isoxadifen
B-730 prosulfocarb isoxadifen
B-731 thiobencarb isoxadifen
B-732 triallate isoxadifen
B-733 bensulfuron-methyl isoxadifen
B-734 bispyribac-sodium isoxadifen
B-735 cyclosulfamuron isoxadifen
B-736 flumetsulam isoxadifen
B-737 flupyrsulfuron-methyl-sodium isoxadifen
B-738 foramsulfuron isoxadifen
B-739 imazamox isoxadifen Herbicide(s) B Safener C
B-740 imazapic isoxadifen
B-741 imazapyr isoxadifen
B-742 imazaquin isoxadifen
B-743 imazethapyr isoxadifen
B-744 imazosulfuron isoxadifen
B-745 iodosulfuron-methyl-sodium isoxadifen
B-746 mesosulfuron isoxadifen
B-747 nicosulfuron isoxadifen
B-748 penoxsulam isoxadifen
B-749 propoxycarbazone-sodium isoxadifen
B-750 pyrazosulfuron-ethyl isoxadifen
B-751 pyroxsulam isoxadifen
B-752 rimsulfuron isoxadifen
B-753 sulfosulfuron isoxadifen
B-754 thiencarbazone-methyl isoxadifen
B-755 tritosulfuron isoxadifen
B-756 2,4-D and its salts and esters isoxadifen
B-757 aminopyralid and its salts and esters isoxadifen
B-758 clopyralid and its salts and esters isoxadifen
B-759 dicamba and its salts and esters isoxadifen
B-760 fluroxypyr-meptyl isoxadifen
B-761 quinclorac isoxadifen
B-762 quinmerac isoxadifen
B-763 H-9 isoxadifen
B-764 diflufenzopyr isoxadifen
B-765 diflufenzopyr-sodium isoxadifen
B-766 clomazone isoxadifen
B-767 diflufenican isoxadifen
B-768 fluorochloridone isoxadifen
B-769 isoxaflutol isoxadifen
B-770 mesotrione isoxadifen
B-771 picolinafen isoxadifen
B-772 sulcotrione isoxadifen
B-773 tefuryltrione isoxadifen
B-774 tembotrione isoxadifen
B-775 topramezone isoxadifen
B-776 H-7 isoxadifen
B-777 atrazine isoxadifen
B-778 diuron isoxadifen Herbicide(s) B Safener C
B-779 fluometuron isoxadifen
B-780 hexazinone isoxadifen
B-781 isoproturon isoxadifen
B-782 metribuzin isoxadifen
B-783 propanil isoxadifen
B-784 terbuthylazine isoxadifen
B-785 paraquat dichloride isoxadifen
B-786 flumioxazin isoxadifen
B-787 oxyfluorfen isoxadifen
B-788 saflufenacil isoxadifen
B-789 sulfentrazone isoxadifen
B-790 H-1 isoxadifen
B-791 H-2 isoxadifen
B-792 glyphosate isoxadifen
B-793 glyphosate-isopropylammonium isoxadifen
B-794 glyphosate-trimesium (sulfosate) isoxadifen
B-795 glufosinate isoxadifen
B-796 glufosinate-ammonium isoxadifen
B-797 pendimethalin isoxadifen
B-798 trifluralin isoxadifen
B-799 acetochlor isoxadifen
B-800 cafenstrole isoxadifen
B-801 dimethenamid-P isoxadifen
B-802 fentrazamide isoxadifen
B-803 flufenacet isoxadifen
B-804 mefenacet isoxadifen
B-805 metazachlor isoxadifen
B-806 metolachlor-S isoxadifen
B-807 pyroxasulfone isoxadifen
B-808 isoxaben isoxadifen
B-809 dymron isoxadifen
B-810 indanofan isoxadifen
B-81 1 oxaziclomefone isoxadifen
B-812 triaziflam isoxadifen
B-813 atrazine + H-1 isoxadifen
B-814 atrazine + glyphosate isoxadifen
B-815 atrazine + mesotrione isoxadifen
B-816 atrazine + nicosulfuron isoxadifen
B-817 atrazine + tembotrione isoxadifen Herbicide(s) B Safener C
B-818 atrazine + topramezone isoxadifen
B-819 clomazone + glyphosate isoxadifen
B-820 diflufenican + clodinafop-propargyl isoxadifen
B-821 diflufenican + fenoxaprop-P-ethyl isoxadifen
B-822 diflufenican + flupyrsulfuron-methyl-sodium isoxadifen
B-823 diflufenican + glyphosate isoxadifen
B-824 diflufenican + mesosulfuron-methyl isoxadifen
B-825 diflufenican + pinoxaden isoxadifen
B-826 diflufenican + pyroxsulam isoxadifen
B-827 flumetsulam + glyphosate isoxadifen
B-828 flumioxazin + glyphosate isoxadifen
B-829 imazapic + glyphosate isoxadifen
B-830 imazethapyr + glyphosate isoxadifen
B-831 isoxaflutol + H-1 isoxadifen
B-832 isoxaflutol + glyphosate isoxadifen
B-833 metazachlor + H-1 isoxadifen
B-834 metazachlor + glyphosate isoxadifen
B-835 metazachlor + mesotrione isoxadifen
B-836 metazachlor + nicosulfuron isoxadifen
B-837 metazachlor + terbuthylazine isoxadifen
B-838 metazachlor + topramezone isoxadifen
B-839 metribuzin + glyphosate isoxadifen
B-840 pendimethalin + H-1 isoxadifen
B-841 pendimethalin + clodinafop-propargyl isoxadifen
B-842 pendimethalin + fenoxaprop-P-ethyl isoxadifen
B-843 pendimethalin + flupyrsulfuron-methyl-sodium isoxadifen
B-844 pendimethalin + glyphosate isoxadifen
B-845 pendimethalin + mesosulfuron-methyl isoxadifen
B-846 pendimethalin + mesotrione isoxadifen
B-847 pendimethalin + nicosulfuron isoxadifen
B-848 pendimethalin + pinoxaden isoxadifen
B-849 pendimethalin + pyroxsulam isoxadifen
B-850 pendimethalin + tembotrione isoxadifen
B-851 pendimethalin + topramezone isoxadifen
B-852 pyroxasulfone + tembotrione isoxadifen
B-853 pyroxasulfone + topramezone isoxadifen
B-854 sulfentrazone + glyphosate isoxadifen
B-855 terbuthylazine + H-1 isoxadifen
B-856 terbuthylazine + foramsulfuron isoxadifen Herbicide(s) B Safener C
B-857 terbuthylazine + glyphosate isoxadifen
B-858 terbuthylazine + mesotrione isoxadifen
B-859 terbuthylazine + nicosulfuron isoxadifen
B-860 terbuthylazine + tembotrione isoxadifen
B-861 terbuthylazine + topramezone isoxadifen
B-862 trifluralin + glyphosate isoxadifen
B-863 clodinafop-propargyl mefenpyr
B-864 cycloxydim mefenpyr
B-865 cyhalofop-butyl mefenpyr
B-866 fenoxaprop-P-ethyl mefenpyr
B-867 pinoxaden mefenpyr
B-868 profoxydim mefenpyr
B-869 tepraloxydim mefenpyr
B-870 tralkoxydim mefenpyr
B-871 esprocarb mefenpyr
B-872 prosulfocarb mefenpyr
B-873 thiobencarb mefenpyr
B-874 triallate mefenpyr
B-875 bensulfuron-methyl mefenpyr
B-876 bispyribac-sodium mefenpyr
B-877 cyclosulfamuron mefenpyr
B-878 flumetsulam mefenpyr
B-879 flupyrsulfuron-methyl-sodium mefenpyr
B-880 foramsulfuron mefenpyr
B-881 imazamox mefenpyr
B-882 imazapic mefenpyr
B-883 imazapyr mefenpyr
B-884 imazaquin mefenpyr
B-885 imazethapyr mefenpyr
B-886 imazosulfuron mefenpyr
B-887 iodosulfuron-methyl-sodium mefenpyr
B-888 mesosulfuron mefenpyr
B-889 nicosulfuron mefenpyr
B-890 penoxsulam mefenpyr
B-891 propoxycarbazone-sodium mefenpyr
B-892 pyrazosulfuron-ethyl mefenpyr
B-893 pyroxsulam mefenpyr
B-894 rimsulfuron mefenpyr
B-895 sulfosulfuron mefenpyr Herbicide(s) B Safener C
B-896 thiencarbazone-methyl mefenpyr
B-897 tritosulfuron mefenpyr
B-898 2,4-D and its salts and esters mefenpyr
B-899 aminopyralid and its salts and esters mefenpyr
B-900 clopyralid and its salts and esters mefenpyr
B-901 dicamba and its salts and esters mefenpyr
B-902 fluroxypyr-meptyl mefenpyr
B-903 quinclorac mefenpyr
B-904 quinmerac mefenpyr
B-905 H-9 mefenpyr
B-906 diflufenzopyr mefenpyr
B-907 diflufenzopyr-sodium mefenpyr
B-908 clomazone mefenpyr
B-909 diflufenican mefenpyr
B-910 fluorochloridone mefenpyr
B-91 1 isoxaflutol mefenpyr
B-912 mesotrione mefenpyr
B-913 picolinafen mefenpyr
B-914 sulcotrione mefenpyr
B-915 tefuryltrione mefenpyr
B-916 tembotrione mefenpyr
B-917 topramezone mefenpyr
B-918 H-7 mefenpyr
B-919 atrazine mefenpyr
B-920 diuron mefenpyr
B-921 fluometuron mefenpyr
B-922 hexazinone mefenpyr
B-923 isoproturon mefenpyr
B-924 metribuzin mefenpyr
B-925 propanil mefenpyr
B-926 terbuthylazine mefenpyr
B-927 paraquat dichloride mefenpyr
B-928 flumioxazin mefenpyr
B-929 oxyfluorfen mefenpyr
B-930 saflufenacil mefenpyr
B-931 sulfentrazone mefenpyr
B-932 H-1 mefenpyr
B-933 H-2 mefenpyr
B-934 glyphosate mefenpyr Herbicide(s) B Safener C
B-935 glyphosate-isopropylammonium mefenpyr
B-936 glyphosate-trimesium (sulfosate) mefenpyr
B-937 glufosinate mefenpyr
B-938 glufosinate-ammonium mefenpyr
B-939 pendimethalin mefenpyr
B-940 trifluralin mefenpyr
B-941 acetochlor mefenpyr
B-942 cafenstrole mefenpyr
B-943 dimethenamid-P mefenpyr
B-944 fentrazamide mefenpyr
B-945 flufenacet mefenpyr
B-946 mefenacet mefenpyr
B-947 metazachlor mefenpyr
B-948 metolachlor-S mefenpyr
B-949 pyroxasulfone mefenpyr
B-950 isoxaben mefenpyr
B-951 dymron mefenpyr
B-952 indanofan mefenpyr
B-953 oxaziclomefone mefenpyr
B-954 triaziflam mefenpyr
B-955 atrazine + H-1 mefenpyr
B-956 atrazine + glyphosate mefenpyr
B-957 atrazine + mesotrione mefenpyr
B-958 atrazine + nicosulfuron mefenpyr
B-959 atrazine + tembotrione mefenpyr
B-960 atrazine + topramezone mefenpyr
B-961 clomazone + glyphosate mefenpyr
B-962 diflufenican + clodinafop-propargyl mefenpyr
B-963 diflufenican + fenoxaprop-P-ethyl mefenpyr
B-964 diflufenican + flupyrsulfuron-methyl-sodium mefenpyr
B-965 diflufenican + glyphosate mefenpyr
B-966 diflufenican + mesosulfuron-methyl mefenpyr
B-967 diflufenican + pinoxaden mefenpyr
B-968 diflufenican + pyroxsulam mefenpyr
B-969 flumetsulam + glyphosate mefenpyr
B-970 flumioxazin + glyphosate mefenpyr
B-971 imazapic + glyphosate mefenpyr
B-972 imazethapyr + glyphosate mefenpyr
B-973 isoxaflutol + H-1 mefenpyr Herbicide(s) B Safener C
B-974 isoxaflutol + glyphosate mefenpyr
B-975 metazachlor + H-1 mefenpyr
B-976 metazachlor + glyphosate mefenpyr
B-977 metazachlor + mesotrione mefenpyr
B-978 metazachlor + nicosulfuron mefenpyr
B-979 metazachlor + terbuthylazine mefenpyr
B-980 metazachlor + topramezone mefenpyr
B-981 metribuzin + glyphosate mefenpyr
B-982 pendimethalin + H-1 mefenpyr
B-983 pendimethalin + clodinafop-propargyl mefenpyr
B-984 pendimethalin + fenoxaprop-P-ethyl mefenpyr
B-985 pendimethalin + flupyrsulfuron-methyl-sodium mefenpyr
B-986 pendimethalin + glyphosate mefenpyr
B-987 pendimethalin + mesosulfuron-methyl mefenpyr
B-988 pendimethalin + mesotrione mefenpyr
B-989 pendimethalin + nicosulfuron mefenpyr
B-990 pendimethalin + pinoxaden mefenpyr
B-991 pendimethalin + pyroxsulam mefenpyr
B-992 pendimethalin + tembotrione mefenpyr
B-993 pendimethalin + topramezone mefenpyr
B-994 pyroxasulfone + tembotrione mefenpyr
B-995 pyroxasulfone + topramezone mefenpyr
B-996 sulfentrazone + glyphosate mefenpyr
B-997 terbuthylazine + H-1 mefenpyr
B-998 terbuthylazine + foramsulfuron mefenpyr
B-999 terbuthylazine + glyphosate mefenpyr
B-1000 terbuthylazine + mesotrione mefenpyr
B-1001 terbuthylazine + nicosulfuron mefenpyr
B-1002 terbuthylazine + tembotrione mefenpyr
B-1003 terbuthylazine + topramezone mefenpyr
B-1004 trifluralin + glyphosate mefenpyr
B-1005 clodinafop-propargyl H-12
B-1006 cycloxydim H-12
B-1007 cyhalofop-butyl H-12
B-1008 fenoxaprop-P-ethyl H-12
B-1009 pinoxaden H-12
B-1010 profoxydim H-12
B-101 1 tepraloxydim H-12
B-1012 tralkoxydim H-12 Herbicide(s) B Safener C
B-1013 esprocarb H-12
B-1014 prosulfocarb H-12
B-1015 thiobencarb H-12
B-1016 triallate H-12
B-1017 bensulfuron-methyl H-12
B-1018 bispyribac-sodium H-12
B-1019 cyclosulfamuron H-12
B-1020 flumetsulam H-12
B-1021 flupyrsulfuron-methyl-sodium H-12
B-1022 foramsulfuron H-12
B-1023 imazamox H-12
B-1024 imazapic H-12
B-1025 imazapyr H-12
B-1026 imazaquin H-12
B-1027 imazethapyr H-12
B-1028 imazosulfuron H-12
B-1029 iodosulfuron-methyl-sodium H-12
B-1030 mesosulfuron H-12
B-1031 nicosulfuron H-12
B-1032 penoxsulam H-12
B-1033 propoxycarbazone-sodium H-12
B-1034 pyrazosulfuron-ethyl H-12
B-1035 pyroxsulam H-12
B-1036 rimsulfuron H-12
B-1037 sulfosulfuron H-12
B-1038 thiencarbazone-methyl H-12
B-1039 tritosulfuron H-12
B-1040 2,4-D and its salts and esters H-12
B-1041 aminopyralid and its salts and esters H-12
B-1042 clopyralid and its salts and esters H-12
B-1043 dicamba and its salts and esters H-12
B-1044 fluroxypyr-meptyl H-12
B-1045 quinclorac H-12
B-1046 quinmerac H-12
B-1047 B-9 H-12
B-1048 diflufenzopyr H-12
B-1049 diflufenzopyr-sodium H-12
B-1050 clomazone H-12
B-1051 diflufenican H-12 Herbicide(s) B Safener C
B-1052 fluorochloridone H-12
B-1053 isoxaflutol H-12
B-1054 mesotrione H-12
B-1055 picolinafen H-12
B-1056 sulcotrione H-12
B-1057 tefuryltrione H-12
B-1058 tembotrione H-12
B-1059 topramezone H-12
B-1060 H-7 H-12
B-1061 atrazine H-12
B-1062 diuron H-12
B-1063 fluometuron H-12
B-1064 hexazinone H-12
B-1065 isoproturon H-12
B-1066 metribuzin H-12
B-1067 propanil H-12
B-1068 terbuthylazine H-12
B-1069 paraquat dichloride H-12
B-1070 flumioxazin H-12
B-1071 oxyfluorfen H-12
B-1072 saflufenacil H-12
B-1073 sulfentrazone H-12
B-1074 H-1 H-12
B-1075 H-2 H-12
B-1076 glyphosate H-12
B-1077 glyphosate-isopropylammonium H-12
B-1078 glyphosate-trimesium (sulfosate) H-12
B-1079 glufosinate H-12
B-1080 glufosinate-ammonium H-12
B-1081 pendimethalin H-12
B-1082 trifluralin H-12
B-1083 acetochlor H-12
B-1084 cafenstrole H-12
B-1085 dimethenamid-P H-12
B-1086 fentrazamide H-12
B-1087 flufenacet H-12
B-1088 mefenacet H-12
B-1089 metazachlor H-12
B-1090 metolachlor-S H-12 Herbicide(s) B Safener C
B-1091 pyroxasulfone H-12
B-1092 isoxaben H-12
B-1093 dymron H-12
B-1094 indanofan H-12
B-1095 oxaziclomefone H-12
B-1096 triaziflam H-12
B-1097 atrazine + H-1 H-12
B-1098 atrazine + glyphosate H-12
B-1099 atrazine + mesotrione H-12
B-1100 atrazine + nicosulfuron H-12
B-1101 atrazine + tembotrione H-12
B-1102 atrazine + topramezone H-12
B-1103 clomazone + glyphosate H-12
B-1104 diflufenican + clodinafop-propargyl H-12
B-1105 diflufenican + fenoxaprop-P-ethyl H-12
B-1106 diflufenican + flupyrsulfuron-methyl-sodium H-12
B-1107 diflufenican + glyphosate H-12
B-1108 diflufenican + mesosulfuron-methyl H-12
B-1109 diflufenican + pinoxaden H-12
B-1110 diflufenican + pyroxsulam H-12
B-1111 flumetsulam + glyphosate H-12
B-1112 flumioxazin + glyphosate H-12
B-1113 imazapic + glyphosate H-12
B-1114 imazethapyr + glyphosate H-12
B-1115 isoxaflutol + H-1 H-12
B-1116 isoxaflutol + glyphosate H-12
B-1117 metazachlor + H-1 H-12
B-1118 metazachlor + glyphosate H-12
B-1119 metazachlor + mesotrione H-12
B-1120 metazachlor + nicosulfuron H-12
B-1121 metazachlor + terbuthylazine H-12
B-1122 metazachlor + topramezone H-12
B-1123 metribuzin + glyphosate H-12
B-1124 pendimethalin + H-1 H-12
B-1125 pendimethalin + clodinafop-propargyl H-12
B-1126 pendimethalin + fenoxaprop-P-ethyl H-12
B-1127 pendimethalin + flupyrsulfuron-methyl-sodium H-12
B-1128 pendimethalin + glyphosate H-12
B-1129 pendimethalin + mesosulfuron-methyl H-12 Herbicide(s) B Safener C
B-1130 pendimethalin + mesotrione H-12
B-1131 pendimethalin + nicosulfuron H-12
B-1132 pendimethalin + pinoxaden H-12
B-1133 pendimethalin + pyroxsulam H-12
B-1134 pendimethalin + tembotrione H-12
B-1135 pendimethalin + topramezone H-12
B-1136 pyroxasulfone + tembotrione H-12
B-1137 pyroxasulfone + topramezone H-12
B-1138 sulfentrazone + glyphosate H-12
B-1139 terbuthylazine + H-1 H-12
B-1140 terbuthylazine + foramsulfuron H-12
B-1141 terbuthylazine + glyphosate H-12
B-1142 terbuthylazine + mesotrione H-12
B-1143 terbuthylazine + nicosulfuron H-12
B-1144 terbuthylazine + tembotrione H-12
B-1145 terbuthylazine + topramezone H-12
B-1146 trifluralin + glyphosate H-12
B-1147 2-1 —
B-1148 2-2 —
B-1149 2-3 —
B-1150 2-4 —
B-1151 2-5 —
B-1152 2-6 —
B-1153 2-7 —
B-1154 2-8 —
B-1155 2-9 —
B-1156 2-1 benoxacor
B-1157 2-2 benoxacor
B-1158 2-3 benoxacor
B-1159 2-4 benoxacor
B-1160 2-5 benoxacor
B-1161 2-6 benoxacor
B-1162 2-7 benoxacor
B-1163 2-8 benoxacor
B-1164 2-9 benoxacor
B-1165 2-1 cloquintocet
B-1166 2-2 cloquintocet
B-1167 2-3 cloquintocet
B-1168 2-4 cloquintocet Herbicide(s) B Safener C
B-1169 2-5 cloquintocet
B-1170 2-6 cloquintocet
B-1171 2-7 cloquintocet
B-1172 2-8 cloquintocet
B-1173 2-9 cloquintocet
B-1174 2-1 cyprosulfamide
B-1175 2-2 cyprosulfamide
B-1176 2-3 cyprosulfamide
B-1177 2-4 cyprosulfamide
B-1178 2-5 cyprosulfamide
B-1179 2-6 cyprosulfamide
B-1180 2-7 cyprosulfamide
B-1181 2-8 cyprosulfamide
B-1182 2-9 cyprosulfamide
B-1183 2-1 dichlormid
B-1184 2-2 dichlormid
B-1185 2-3 dichlormid
B-1186 2-4 dichlormid
B-1187 2-5 dichlormid
B-1188 2-6 dichlormid
B-1189 2-7 dichlormid
B-1190 2-8 dichlormid
B-1191 2-9 dichlormid
B-1192 2-1 fenchlorazole
B-1193 2-2 fenchlorazole
B-1194 2-3 fenchlorazole
B-1195 2-4 fenchlorazole
B-1196 2-5 fenchlorazole
B-1197 2-6 fenchlorazole
B-1198 2-7 fenchlorazole
B-1199 2-8 fenchlorazole
B-1200 2-9 fenchlorazole
B-1201 2-1 isoxadifen
B-1202 2-2 isoxadifen
B-1203 2-3 isoxadifen
B-1204 2-4 isoxadifen
B-1205 2-5 isoxadifen
B-1206 2-6 isoxadifen
B-1207 2-7 isoxadifen Herbicide(s) B Safener C
B-1208 2-8 isoxadifen
B-1209 2-9 isoxadifen
B-1210 2-1 mefenpyr
B-121 1 2-2 mefenpyr
B-1212 2-3 mefenpyr
B-1213 2-4 mefenpyr
B-1214 2-5 mefenpyr
B-1215 2-6 mefenpyr
B-1216 2-7 mefenpyr
B-1217 2-8 mefenpyr
B-1218 2-9 mefenpyr
B-1219 2-1 H-1 1
B-1220 2-2 H-1 1
B-1221 2-3 H-1 1
B-1222 2-4 H-1 1
B-1223 2-5 H-1 1
B-1224 2-6 H-1 1
B-1225 2-7 H-1 1
B-1226 2-8 H-1 1
B-1227 2-9 H-1 1
B-1228 2-1 H-12
B-1229 2-2 H-12
B-1230 2-3 H-12
B-1231 2-4 H-12
B-1232 2-5 H-12
B-1233 2-6 H-12
B-1234 2-7 H-12
B-1235 2-8 H-12
B-1236 2-9 H-12
The compounds of formula I and the compositions according to the invention may also have a plant-strengthening action. Accordingly, they are suitable for mobilizing the defense system of the plants against attack by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances which are capable of stimulating the defense system of treated plants in such a way that, when subsequently inoculated by unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms. The compounds of formula I can be employed for protecting plants against attack by unwanted microorganisms within a certain period of time after the treatment. The period of time within which their protection is effected generally extends from 1 to 28 days, preferably from 1 to 14 days, after the treatment of the plants with the compounds of formula I, or, after treatment of the seed, for up to 9 months after sowing.
The compounds of formula I and the compositions according to the invention are also suitable for increasing the harvest yield.
Moreover, they have reduced toxicity and are tolerated well by the plants. The following examples will further illustrate the invention:
With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds obtained in this manner are listed in the tables that follow, together with physical data. The products shown below were characterized by determination of the melting point, NMR spectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.
HPLC-MS = high performance liquid chromatography coupled with mass spectrometry;
HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; mobile phase: acetonitrile + 0.1 % trifluoroacetic acid (TFA)/water + 0.1 % TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40 °C, flow rate 1.8 ml/min.
MS: quadrupole electrospray ionization, 80 V (positive mode).
HPLC column: Luna-C18(2) 5 μ m column (Phenomenex), 2.0*50 mm; mobile phase: ac- etonitrile + 0.0625% trifluoroacetic acid (TFA)/water + 0.0675% TFA, using a gradient from 10:90 to 80:20 over 4.0 minutes at 40 °C, flow rate 0.8 ml/min.
MS: quadrupole electrospray ionization, 70 V (positive mode).
EtOAc: acetic acid ethyl ester
THF: tetrahydrofuran
LiHMDS: lithium bis(trimethylsilyl)amide
m-CPBA: 3-chloroperoxybenzoic acid
TFA: trifluoroacetic acid
Working Example
Synthesis of 4-methyl-1 ,2,4-triazol-3-amine
Figure imgf000147_0001
A solution of 1 -aminoguanidine-hydrochloride (50 g, 0.45 mol) and MeNCS (280 g, 3.8 mol) in EtOH (500 ml) was stirred in an autoclave at 150 °C for 4 hours. After this time, it was cooled to 25 °C, concentrated, re-dissolved in water (700 mL) and K2CO3 (62.5 g, 0.55 mol) was added. The reaction mixture was stirred under reflux for 16 hours and the reaction was cooled to 25 °C. The solvent was removed under vacuum to give the crude, which was dissolved in MeOH and filtered. The filtrate was concentrated. The residue was purified by column chromatography on silica gel column eluted with DCM: MeOH (30:1 to 10:1 to 5:1 ) to give the 3-amino- 4-methyl-1 H-1 ,2,4-triazole-5-thione (20 g, 31 %) as a white solid.
To a solution of 3-amino-4-methyl-1 H-1 ,2,4-triazole-5-thione (25 g, 0.2 mol) in DCM (300 mL) was added a solution of H2O2 (86 g, 0.6 mol, 30%) in CH3COOH (150 mL) at 0-5 °C. The reaction mixture was stirred at 25 °C for 4 hours. The reaction mixture was quenched by adding a saturated aqueous solution of Na2S03 and a aqueous solution of NaOH until pH 10. The aqueous layer was separated and concentrated under vacuum to give the crude product. The product was dissolved in a DCM : MeOH = 10 : 1 (30 mL) mixture and the remaining solid was discarded. The solvent was removed to give 4-methyl-1 ,2,4-triazol-3-amine (5 g, 23%) as a white solid. H NMR (MeOD, 400MHz): δ 3.47 (s, 3 H) 7.91 (s, 1 H).
Following the same procedure, 4-ethyl-1 ,2,4-triazol-3-amine was also obtained
N H HCI
[I
Figure imgf000147_0002
H NMR (MeOD, 400MHz): δ 1 .36 (t, J=7.2 Hz, 3 H) 3.87 (q, J=7.2 Hz, 2 H) 7.98 (s, 1
Synthesis of 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoylchloride
Figure imgf000147_0003
2,6-dichloro-4-fluoro-aniline (12 g, 67 mmol) was taken up in concentrated HCI (13 mL) and water (51 mL) at 0 °C. After stirring for 15 min, a solution of NaN02 (4.85 g, 70.3 mmol) in water (10 mL) was added drop-wise at 0 °C and the mixture was stirred for 45 min. A solution of MeSNa (35 g, 100 mmol) and Na2C03 (10.6 g, 100 mmol) in water (100 mL) was then added to the above solution drop-wise at 50 °C. After addition, the mixture was stirred for 1 hour, then extracted with EtOAc and the combined organic layers were dried (MgSC ), filtered and the filtrate concentrated in vacuo to give the crude product. Flash chromatography using neat 60-90 petrol ether afforded 1 ,3-dichloro-5-fluoro-2-methylsulfanyl-benzene (4.7 g, 34%). H NMR (CDCIs, 400MHz): 57.17 (d, 2H), 2.41 (s, 3H). To a solution of 1 ,3-dichloro-5-fluoro-2-methylsulfanyl-benzene (4.7 g, 22.5 mmol) in anhydrous THF (100 mL) was added BuLi.THF (15 mL, 44.5 mmol, 3.0 M) drop-wise at - 78 °C under a nitrogen atmosphere. After stirring for 50 min, dry ice was added and the mixture was allowed to warm to ambient temperature. The reaction was quenched by addition of sat. aqueous NH4CI and extracted with EtOAc. The combined organic layers were dried (MgSC ), filtered and the filtrate concentrated in vacuo to afford 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoic acid (3.6 g, 63%). H NMR (CDCIs, 400MHz): δ 7.30 (d, 1 H), 2.44 (s, A mixture of 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoic acid (750 mg, 2.95 mmol) and
(COCI)2 (1 .13 g, 8.86 mmol) in CH2CI2 (10 mL) was stirred for 2 hours at 0 °C. The solvent was evaporated under reduced pressure to afford 2,4-dichloro-6-fluoro-3-methylsulfanyl- benzoylchloride used as the crude product (750 mg).
Synthesis of 2,4-dichloro-3-ethoxy-6-fluoro-benzoyl chloride
Figure imgf000148_0001
To a solution of 2,6-dichloro-4-fluoro-phenol (2 g, 1 1 .1 1 mmol) in 20 mL anhydrous DMF was added K2CO3 (3.07 g, 22.22 mmol) at room temperature. After stirring for 30 min, Etl (3.47 g, 22.22 mmol) was added and the mixture was stirred at room temperature overnight. Water was added and the product was extracted with MTBE. The organic phase was washed with brine, dried and concentrated in vacuum to give the crude product, which was purified by column chromatography eluted with 100 % cyclohexane to afford 1 ,3-dichloro-2-ethoxy-5-fluoro- benzene (1 .5 g, 64.9 %). H NMR (CDCI3, 400MHz): δ 1 .46 (t, J=7.03 Hz, 3 H) 4.07 (q, J=7.03 Hz, 2 H) 7.07 (d, J=7.78 Hz, 2 H). To a solution of diisopropylamine (1.5 mL, 10.5 mmol) in 10 mL anhydrous THF was added n-BuLi (3.5 mL, 8.75 mmol) dropwise at 0 °C under nitrogen and the mixture was stirred 30 min at 0 °C. To 1 ,3-dichloro-2-ethoxy-5-fluoro-benzene (1.5 g, 7.21 mmol) in 30 mL anhydrous THF was added, dropwise, the freshly prepared LDA solution at -78 °C under nitrogen and the mixture was stirred for 1 .5 hours. Then dry ice was added and the reaction was let to warm to room temperature. The reaction was quenched with sat. NH4CI solution and THF was evaporated. Water was added to the residue and it was basified with a saturated NaHC03 solution, extracted twice with DCM. Then the aqueous layer was acidified with 3N HCI to pH 1 and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated in vacu- urn to give 2,4-dichloro-3-ethoxy-6-fluoro-benzoic acid (1 g, 55.0 %).
1 H NMR (CDCI3, 400MHz): δ 1 .49 (t, J=7.03 Hz, 3 H) 4.10 (q, J=7.03 Hz, 2 H) 7.20 (d, J=8.53 Hz, 1 H). To a solution of 2,4-dichloro-3-ethoxy-6-fluoro-benzoic acid (300 mg, 1 .19 mmol) in 15 mL anhydrous DCM was added (COCI)2 (0.17 mL, 1.79 mmol) and 1 drop of DMF at 0 °C. The mixture was stirred at room temperature for 2 hrs. The solution was concentrated in vacuum to afford 2,4-dichloro-3-ethoxy-6-fluoro-benzoyl chloride used directly in the next step (300 mg) Example 1 : Preparation of 2,4-dichloro-6-fluoro-3-methylsulfanyl-N-(4-methyl-1 ,2,4-triazol-
3-yl)benzamide (cpd. 4).
Figure imgf000149_0001
To a solution of 4-methyl-1 ,2,4-triazol-3-amine (100 mg, 1.02 mmol) in 50 mL anhydrous THF was added n-BuLi (1.5 mL, 3.06 mmol) at -78 °C under nitrogen. After stirring for 30 min, 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoylchloride (200 mg, 1 .02 mmol) in 5 mL THF was added and the mixture was stirred for 2 hours at this temperature and was let to warm to room temperature. The reaction was quenched by adding a NH4CI solution (20 mL), extracted with EtOAc (20 mL * 3). The combined organic layers were combined, dried over Na2S04, filtered and concentrated to give the crude product which was purified by prep-HPLC (25 mg, 8.36 %, M+1 =336). H NMR (MeOD, 400MHz): δ 2.41 (s, 3 H) 3.71 (s, 3 H) 7.55 (d, J=9.2 Hz, 1 H) 8.53 (s, 1
Example 2: Preparation of 2,4-dichloro-6-fluoro-3-methylsulfonyl-N-(4-methyl-1 ,2,4-triazol- 3-yl)benzamide (cpd. 5).
Figure imgf000150_0001
To a solution of 2,4-dichloro-6-fluoro-3-methylsulfanyl-N-(4-methyl-1 ,2,4-triazol-3- yl)benzamide (170 mg, 0.49 mmol) in 5 mL anhydrous DCM was added m-CPBA (260 mg, 1.47 mmol) at 0 °C. The mixture was stirred for 2 days at room temperature. Then the organic layer was quenched by a adding a saturated Na2SC"3 solution. The organic layer was washed with a sat. NaHC03 solution twice, dried over Na2S04 and concentrated to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-6-fluoro-3-methylsulfonyl-N-(4-methyl- 1 ,2,4-triazol-3-yl)benzamide (128 mg, 48.5 %, M+1 =367). H NMR: (MeOD, 400MHz): δ 3.39 (s, 3 H) 3.64 (s, 3 H) 7.67 (d, J=8.0 Hz, 1 H) 8.43 (s,
1 H).
Example 3: Preparation of 2,4-dichloro-N-(4-ethyl-1 ,2,4-triazol-3-yl)-6-fluoro-3 methyl- sulfanyl-benzamide (cpd. 3).
Figure imgf000150_0002
To a solution of 4-ethyl-1 ,2,4-triazol-3-amine (350 mg, 3.12 mmol) in 50 mL anhydrous THF was added LiHMDS (15 mL, 12.4 mmol) at -78 °C under nitrogen. After stirring for 15 min, 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoylchloride (843 mg, 3.57 mmol) in 5 mL THF was added and the mixture was stirred for 2 hours at this temperature and let to warm to room temperature. The reaction was quenched by adding a saturated NH4CI solution (50 mL), extracted with EtOAc (50 mL * 3). The combined organic layers were combined, dried over Na2S04, filtered and concentrated to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-N-(4-ethyl-1 ,2,4-triazol-3-yl)-6-fluoro-3 methyl-sulfanyl-benzamide (90 mg, 8.36 %, M+1 =349). H NMR (MeOD 400MHz): δ 1 .43 (t, J=7.6 Hz, 3 H) 2.41 (s, 3 H) 4.06 (q, J=7.2 Hz, 2 H) 7.50 (d, J=8.8 Hz, 1 H) 8.47 (s,1 H).
Example 4: Preparation of 2,4-dichloro-N-(4-ethyl-1 ,2,4-triazol-3-yl)-6-fluoro-3-methyl- sulfonyl-benzamide (cpd. 2).
Figure imgf000150_0003
To a solution of 2,4-dichloro-N-(4-ethyl-1 ,2,4-triazol-3-yl)-6-fluoro-3 methyl-sulfanyl- benzamide (170 mg, 0.49 mmol) in 5 mL anhydrous DCM was added m-CPBA (260 mg,
1 .47 mmol) at 0 °C. The mixture was stirred for 2 days at room temperature. Then the reaction was quenched by adding a saturated Na2S03 solution. The organic layer was washed with a sat. NaHCOs solution twice, dried over Na2S04 and concentrated to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-N-(4-ethyl-1 ,2,4-triazol-3-yl)-6- fluoro-3-methyl-sulfonyl-benzamide (90 mg, 47.5 %, M+1 =381 ). H NMR( MeOD 400MHz): δ 1 .44 (t, J=7.2 Hz, 3 H) 3.89 (s, 3 H) 4.08 - 4.09 (m, 2 H) 7.66 (s, 1 H) 8.56 (s, 1 H).
Example 5: Preparation of 2,4-dichloro-3-ethoxy-N-(4-ethyl-1 ,2,4-triazol-3-yl)-6-fluoro- benzamide (cpd. 7).
Figure imgf000151_0001
To a solution of 4-ethyl-1 ,2,4-triazol-3-amine (134mg, 1 .20 mmol) in 60 mL anhydrous
THF was added LiHMDS (3.6 mL, 3.6 mmol) at -78 °C under nitrogen and the mixture was allowed to warm to -40 °C. After stirred for 3 hours, the mixture was cooled to -78 °C and was added to a solution of 2,4-dichloro-3-ethoxy-6-fluoro-benzoyl chloride in 15 mL THF. The mixture was stirred at room temperature overnight. The reaction was quenched by adding a NH4CI solution (150 mL), extracted with EtOAc. The organic phase was washed with brine, dried and concentrated in vacuum to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-3-ethoxy-N-(4-ethyl-1 ,2,4-triazol-3-yl)-6-fluoro-benzamide (220 mg, 53.0 %, M+1 =347). 1H NMR: (MeOD 400MHz): δ 1 .45 (t, J=7.03 Hz, 6 H) 3.88 - 4.30 (m, 4 H) 7.42 (d, J=8.53
Hz, 1 H) 8.53 (s, 1 H).
By analogy to the methods described in the Examples above, the following compounds of formula I according to Table 21 1 were prepared:
Table 21 1
Figure imgf000152_0001
Figure imgf000152_0002
Use examples
The herbicidal activity of the compunds of the formula I was demonstrated by the following greenhouse experiments:
The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.
For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform ger- mination of the test plants, unless this has been impaired by the active ingredients.
For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
Depending on the species, the plants were kept at 10-25°C or 20-35°C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or nor- mal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
The plants used in the greenhouse experiments belonged to the following species:
Figure imgf000153_0001
Following representative compounds of formula I according to Table 21 1 were used in post- emergence treatments in greenhouse experiments (values labeled with * result from pre- emergence experiments):
Table 212: treatment damage [%]in weed species
cpd. no. [g/ha] I II III IV V VI VII VIII
1 2 1000 100 - 75, 95* 80* 75 90, 98* 85* 100
2 3 1000 100, 90* - 100, 90* - 80 98, 75* 70* 100
3 4 1000 100, 70* 90 100, 100* 70* 90 95 70* 100
4 5 1000 98, 80* 85 90, 85* 70* - 98, 80* 85* 95

Claims

We claim:
1 . N-(1 ,2,4-triazol-3-yl)arylcarboxamides of formula I,
Figure imgf000154_0001
wherein is selected from the group consisting of cyano-Z1, halogen, nitro, Ci-Cs-alkyl, C2-C8- alkenyl, C2-C8-alkynyl, C3-Cio-cycloalkyl-Z1, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C3- Cs-haloalkynyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Z1, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1, and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different;
X is N or CR2;
R2, R3 are identical or different and independently selected from the group consisting of hydrogen, halogen, OH-Z2, NO2-Z2, cyano-Z2, Ci-C6-alkyl, C2-Cs-alkenyl, C2-C8- alkynyl, C3-Cio-cycloalkyl-Z2, C3-Cio-cycloalkoxy-Z2, where the C3-Cio-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or complete- ly halogenated, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, Cs-Cs-haloalkynyl, d-Cs-alkoxy-
Z2, Ci-Cs-haloalkoxy-Z2, C3-Cio-cycloalkyl- Ci-C2-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy- Z2, Ci-C4-alkylthio-Ci-C4-alkylthio-Z2, C2-C8-alkenyloxy-Z2, C2-C8-alkynyloxy-Z2, C2- Cs-haloalkenyloxy-Z2, Cs-Cs-haloalkynyloxy-Z2, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z2, (tri-Ci-C4-alkyl)silyl-Z2, R2b-S(0)k-Z2, R2c-C(=0)-Z2, R2dO-C(=0)-Z2, R2dO-N=CH-Z2,
Figure imgf000154_0002
R2eR2f N-C(=0)-Z2, R¾R2hN-Z2, phenyl-Z2a and heterocy- clyl-Z2a, where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10- membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z2a and heterocy- clyl-Z2a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R21, which are identical or different; or and R3 together form a saturated 5- or 6-membered ring, optionally containing an oxygen or a S(0)n heteroatom, the 5- or 6-membered ring being unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy; is selected from the group consisting of hydrogen, cyano- Z1, halogen, nitro, Ci-Cs- alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci- C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, d-Cs-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phe- noxy-Z1 and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different; is selected from the group consisting of cyano- Z1, halogen, nitro, Ci-Cs-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4- alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1 and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different; is selected from the group consisting of hydrogen, CN, nitro, hydroxy, amino, C1-C6- alkyl, Ci-C6-cya no-alkyI, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylcarbonyl, Ci-C6-alkyaminocarbonyl, Ci-C6-dialkyl-aminocarbonyl, Ci-C6-alkyamino, C1-C6- dialkyl-amino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C -alkyl, RbRbN-S(0)n-Z, R O-S(0)n- Z, Rb-S(0)n-Z, RcRcN-Ci-C3-alkyl-S(0)n-Ci-C3-alkyl,
Figure imgf000156_0001
Rd- C(=0)0-Ci-C3-alkyl , Rd-0-C(=0)0-Ci-C3-alkyl ,RdO-C(=0)-Ci-C3-alkyl, ReRfN- C(=0)-Ci-C3-alkyl,
Figure imgf000156_0002
R -S(0)n-ReN-Ci-C3-alkyl, RCRCN-Ci- C3-alkyl, phenyl-Z and heterocyclyl-Z, where heterocyclyl is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups R', which are identical or different;
R7 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy, Ci- C4-alkoxy-Ci-C4-alkyl and Ci-C4-haloalkoxy-Ci-C4-alkyl; n is 0, 1 or 2; k is O, 1 or 2;
R', R11 , R21 independently of each other are selected from the group consisting of
halogen, NO2, CN, d-Ce-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, Ci-Ce- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, d-Ce-alkoxy, Ci-C -alkoxy-Ci-C -alkyl, Ci-C -alkylthio-Ci-C -alkyl, Ci-C - haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C3-C7-cycloalkoxy and Ci- C6-haloalkyloxy, or two vicinal radicals R', R11 or R21 together may form a group =0;
Z, Z Z2 independently of each other are selected from the group consisting of a
covalent bond and Ci-C4-alkanediyl;
Z2a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O- Ci-C4-alkanediyl, Ci-C4-alkanediyl-0 and
Ci-C4-alkanediyl-0-Ci-C4-alkanediyl;
Rb, R1 b, R2b independently of each other are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
Rc, R2c independently of each other are selected from the group consisting of
hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; Rd, R2d independently of each other are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
Re, Rf independently of each other are selected from the group consisting of
hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, or
Re, Rf together with the nitrogen atom, to which they are bound may form a 5-, 6 or
7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R2e, R2f independently of each other have the meanings given for Re, Rf;
R9 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, C1-C4- alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy;
Rh is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, C1-C4- alkylcarbonyl, a radical C(=0)-Rk, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or
R9, Rh together with the nitrogen atom, to which they are bound may form a 5-, 6 or
7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R¾, R2h independently of each other have the meanings given for Rs, Rh;
Rk has the meanings given for Rc; an N-oxide or an agriculturally suitable salt thereof.
The compound as claimed in claim 1 , where R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci- C4-haloalkylthio and Ci-C4-alkylsulfonyl.
The compound as claimed in claim 1 or 2, where X is N.
The compound as claimed in claim 1 or 2, where X is CR2 and R2 is different from hydro gen.
The compound as claimed in claim 1 or 2, where X is CR2 and R2 is hydrogen.
The compound as claimed in claim 4, where R2 is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, C1-C4- alkoxycarbonyl, Ci-C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl.
The compound as claimed in any one of the preceding claims, where R3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylS(0)2 and C1-C4- haloalkyl-S(0)2.
The compound as claimed in any one of the preceding claims, where R4 is selected from the group consisting of hydrogen, CHF2, CF3, CN, NO2, CH3 and halogen.
The compound as claimed in any one of the preceding claims, where R5 is selected from the group consisting of CHF2, CF3 and halogen. 10. The compound as claimed in any one of the preceding claims, where R5 is selected from the group consisting of chlorine and fluorine.
1 1 . The compound as claimed in any one of the preceding claims, where R6 is hydrogen. 12. The compound as claimed in any one of the preceding claims, where R6 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy- Ci-C4-alkyl,
Figure imgf000159_0001
phenyl-Z and where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups R', which are identical or different.
3. The compound as claimed in any one of the preceding claims, where R7 is selected from the group consisting of Ci-C4-alkyl, C3-C7-cycloalkyl, Ci-C4-haloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C4-alkoxy and Ci-C4-alkoxy-Ci-C4-alkyl.
4. The compound as claimed in claiml , where X is CR2 and the variables R1 , R2, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkyl-S(0)2;
R2 is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci- C4-alkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6- alkynyloxy, C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci- C4-alkyl-S(0)k and Ci-C4-haloalkyl-S(0)k, where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl;
R3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and Ci-C4-alkyl-S(0)2;
R4 is selected from the group consisting of hydrogen and halogen;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci- C2-alkyl;
R7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy- Ci-C2-alkyl.
5. The compound as claimed in claim 1 , where X is CR2 and the variables R1 , R2, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl;
R2 is selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methylsulfonyl, methylsulfinyl, methylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 5- isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5-isoxazolyl;
R3 is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl;
R4 is selected from the group consisting of hydrogen, chlorine and fluorine;
R5 is selected from the group consisting of chlorine and fluorine; R6 is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl;
R7 is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxymethyl, methoxyethyl and ethoxymethyl;
16. The compound as claimed in claim 1 , where X is N and the variables R1, R3, R4,R5, R6 and R7 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, cyclopropyl, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and
Ci-C4-alkyl-S(0)2;
R3 is selected from the group consisting of hydrogen, halogen, CN, Ci-C4-haloalkyl and
Ci-C4-alkyl-S(0)2;
R4 is selected from the group consisting of hydrogen and halogen;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl and phenyl-Ci-
C2-alkyl;
R7 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C2-alkoxy- Ci-C2-alkyl.
17. The compound as claimed in claim 1 , where X is N and the variables R1, R3, R4,R5, R6 and R7 have the following meanings: R1 is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl;
R3 is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl;
R4 is selected from the group consisting of hydrogen, chlorine and fluorine;
R5 is selected from the group consisting of chlorine and fluorine; R6 is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2- enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl;
R7 is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxymethyl, methoxyethyl and ethoxymethyl;
A composition comprising at least one compound as claimed in any one of claims 1 to 17 and at least one auxiliary, which is customary for formulating crop protection compounds.
The use of a compound as claimed in any one of claims 1 to 17 or a composition of claim 26 for controlling unwanted vegetation.
20. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound as claimed in any one of claims 1 to 17 or a composition of claim 18 to act on plants, their seed and/or their habitat.
PCT/EP2014/064531 2013-07-18 2014-07-08 Substituted n-(1,2,4-triazol-3-yl)arylcarboxamide compounds and their use as herbicides WO2015007564A1 (en)

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