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WO2014184074A1 - Composés de n-(tétrazol-5-yl)- et n-(triazol-5-yl)hétarylcarboxamide substitués et leur utilisation en tant qu'herbicides - Google Patents

Composés de n-(tétrazol-5-yl)- et n-(triazol-5-yl)hétarylcarboxamide substitués et leur utilisation en tant qu'herbicides Download PDF

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WO2014184074A1
WO2014184074A1 PCT/EP2014/059378 EP2014059378W WO2014184074A1 WO 2014184074 A1 WO2014184074 A1 WO 2014184074A1 EP 2014059378 W EP2014059378 W EP 2014059378W WO 2014184074 A1 WO2014184074 A1 WO 2014184074A1
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alkyl
alkoxy
group
haloalkyl
compound
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Inventor
Helmut Kraus
Frederick CALO
Matthias Witschel
Thomas Seitz
Trevor William Newton
Dario MASSA
Thomas Mietzner
Maciej Pasternak
Klaus Kreuz
Richard Roger Evans
Jens Lerchl
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to substituted N-(tetrazol-5-yl)- and N-(triazol-5- yl)hetarylcarboxamide compounds and the N-oxides and salts thereof and to compositions comprising the same.
  • the invention also relates to the use of the N-(tetrazol-5-yl)- and N- (triazol-5-yl)hetarylcarboxamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying such compounds.
  • WO 201 1/035874 describes N-(1 ,2,5-oxadiazol-3-yl)benzamides carrying 3 substituents in the 2-, 3- and 4-positions of the phenyl ring and their use as herbicides.
  • 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 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-(tetrazol-5-yl)- and N-(triazol-5-yl)hetarylcarboxamide 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-(tetrazol-5-yl)- and N-(triazol-5-yl)hetarylcarboxamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.
  • B is N or CH
  • X 1 is N or CR 1
  • X 2 is N or CR 2
  • X 3 is N or CR 3
  • X 4 is N or CR 4
  • X 1 , X 3 and X 4 is N;
  • R is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C 3 - C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C4- alkoxy-Ci-C 4 -alkyl, Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, R b -S(0) n -Ci-C 3 -alkyl,
  • Cs-alkyl, R d O-C( 0)-Ci-C 3 -alkyl, R9R h N-Ci-C 3 -alkyl, phe- nyl-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 heterocy- cle, 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 1 is selected from the group consisting of cyano-Z 1 , halogen, nitro, Ci-C 8 -alkyl, C2-C8- alkenyl, C2-C 8 -alkynyl, Ci-C 8 -haloalkyl, d
  • 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-C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 - alkynyl, C 3 -Cio-cycloalkyl-Z 2 , C 3 -Cio-cycloalkoxy-Z 2 , where the C 3 -Cio-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C 8 -haloalkyl, Ci-C 8 -alkoxy-Z 2 , Ci-C 8 -haloalkoxy-Z 2 , Ci-C 4 -alkoxy- Ci-C 4 -alkoxy-Z 2 , Ci-C 4 -alkylthio-Ci-C 4 -alkylthio-Z 2 ,
  • R 4 , R 5 are identical or different and independently 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-C8- alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino- S(0)k, Ci-C3-alkylcarbonyl, d-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C 4 -alkoxy-Z 1 , Ci-C 4
  • 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 R 11 , which are identical or different;
  • R 5 is not hydrogen, halogen, cyano, nitro, Ci-C4-alkyl or C1-C4- haloalkyl; and further provided that if X 4 is CR 4 and R 4 is hydrogen, halogen, cyano, nitro, Ci-C4-alkyl or Ci-C4-haloalkyl, R 5 is not hydrogen, halogen, cyano, nitro, Ci-
  • n 0, 1 or 2;
  • k 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
  • Ci-C4-alkanediyl-0-Ci-C4-alkanediyl; 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- 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
  • 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
  • Ci-C4-alkyl Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • 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-
  • 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, 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, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-al
  • R9, R h together with the nitrogen atom, to which they are bound may form a 5-, 6- or
  • R3 ⁇ 4, R 2h independently of each other have the meanings given for Rs, R h ;
  • R k has the meanings given for R c ;
  • Z ⁇ has one of the meanings given for Z;
  • R ⁇ 2 has one of the meanings given for R b ;
  • R ⁇ 3 has one of the meanings given for R c ;
  • Rq4 ; Rqs independently of each other have the meanings given for Rs, R h ; R ⁇ 6 has one of the meanings given for R';
  • 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 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 present invention also relates to the use of a composition according to the invention including an N-oxide or an agriculturally suitable salt thereof for combating or controlling unwanted vegetation.
  • 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 of compounds I can in particular be prepared by oxidizing the ring nitrogen atom(s) of the oxadiazole ring or the ring nitrogen atom(s) of the six-membered aromatic ring with a suitable oxidizing agent, such as peroxocarboxylic acids or other peroxides.
  • 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 non- radioactive 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 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 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, Ci-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, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltnmethylammonium 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,
  • 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 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 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 haloalkyi.
  • alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyi) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, e.g. from 1 to 8 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
  • C1-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 - methylpropyl and
  • Ci-Cio-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5- methylhexyl, 1 -ethyl pentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1 -methyloctyl, 2-methylheptyl, 1 - ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propyl pentyl, 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.
  • haloalkyi as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi 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 (“Ci- C6-haloalkyl”), more frequently 1 to 4 carbon atoms (“Ci-Cio-haloalkyl”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.
  • haloalkyi as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi group, e.g.
  • haloalkyi moieties 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.
  • C1-C2- fluoroalkyl examples include fluoromethyl, 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,
  • cycloalkyl as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C3-C10- 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
  • 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-difluorocyclopentyl and the like.
  • 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
  • cyclopropylmethyl cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutyl propyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, 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 may be 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 (“C 2 -C 6 -haloalkenyl”) or 2 to 4 (“C2-C 4 -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 hydrocarbon radicals having usually 2 to 8 (“C2-C8-alkynyl”), frequently 2 to 6 (“C2-C6-alkynyl”), preferably 2 to 4 carbon atoms (“C2-C 4 -alkynyl”) and a triple bond in any position, for example C2-C 4 -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 may be 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 ("d-Cs-haloalkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-haloalkoxy”), preferably 1 to 4 carbon atoms (“Ci- 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, OCHF 2 , OCF 3 , OCH 2 CI, 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 -(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, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • 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- (l -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-methyl
  • 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, difluoromethoxymethyl, 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,
  • 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
  • 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-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2CI, SCHCI2, SCCI3, 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
  • 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 -C2-a I kylsu If i nyl refers to a Ci-C2-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-a I kylsu If i nyl refers to a Ci- C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • 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, 2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2- methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 ,1 -dimethylbutylsulfinyl,
  • 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
  • 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 -NHR * , 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-NR * R°, 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, diethylamino, 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 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, pyrimidyl 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, tetrahydrothien-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, imidazolidin-4-y
  • 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-
  • tetrahydropyridazinyl 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3, 5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl
  • Examples of a 5- or 6-membered monocyclic aromatic heterocyclic ring 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
  • 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, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, isochinolinyl, 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, tautomer 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 a N- oxide or an agriculturally suitable salt thereof.
  • Particularly preferred compounds according to the invention are compounds of formula I or an agriculturally suitable salt thereof.
  • variable B in the compounds of formula I is CH.
  • R c is hydrogen, Ci-C6-alkyl C3-C7-cycloalkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, Ci-C6-haloalkyl or phenyl, in particular Ci-C 4 -alkyl or Ci-C 4 -haloalkyl;
  • R d is Ci-C6-alkyl or Ci-C6-haloalkyl, in particular Ci-C 4 -alkyl,
  • R e , R f are independently of each other selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and benzyl, and in particular from the group consisting of hydrogen and Ci-C 4 -alkyl, or R e , R f 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 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 and Ci-C4-haloalkyl, and in particular 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
  • R9, R h are independently of each other selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and benzyl and in particular from the group consisting of hydrogen or Ci-C4-alkyl, or
  • R k is H, Ci-C4-alkyl, Ci-C4-haloalkyl or phenyl, in particular Ci-C4-alkyl.
  • R c , R d , R e , R f and R k are as defined above and which preferably have on their own or in particular in combination the following meanings:
  • 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, and
  • R k is Ci-C 4 -alkyl.
  • variable R in the compounds of formula I is selected from Ci-C4-alkyl, C3-C7-cycloalkyl, Ci-C4-haloalkyl and C1-C4- alkoxy-Ci-C4-alkyl, in particular from methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, CF 3 , CHF 2 , CCIF 2 , CH 2 CF 3 , CF 2 CF 3 , CH 2 CI, CHCI 2 , ethoxyethyl, ethoxymethyl, methoxyethyl and methoxymethyl.
  • variable R in the compounds of formula I is selected from Ci-C4-alkyl, C3-C7-cycloalkyl, Ci-C4-haloalkyl, methox- yethyl and methoxymethyl, in particular from methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cy- clopentyl, cyclohexyl, CF 3 , CHF 2 , CCIF 2 , CH 2 CF 3 , CF 2 CF 3 , CH 2 CI, CHCI 2 , methoxyethyl and methoxymethyl.
  • variable R in the com- pounds of formula I is phenyl or heterocyclyl, 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 as defined above and which are independently from one another are preferably selected from the group consisting of halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl and C1-C6- haloalkyloxy, more preferably from
  • variable R in the compounds of formula I is phenyl or heterocyclyl, where heterocyclyl is a partially unsaturated or aromatic 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the bicyclic heterocycle consists of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring, and where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups R' which independently from one another have the aforementioned preferred meanings.
  • variable R in the compounds of the formula I is phenyl or heterocyclyl selected from pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, piperidin- 2-yl, piperidin-3-yl, piperidin-4-yl, benzisoxazole-2-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-triazol-3-yl, 1 - ethylbenzimidazol-2-yl, 4-methylthiazol-2-yl, thiophen-2-yl, furan-2-yl, furan-3-yl, tetrahydrofu- ran-2-yl, tetrahydrofuran-3-yl, isoxazol-2-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, oxazol-2- yl, oxazol-3-yl, o
  • variable R in the compounds of formula I is R b -S(0) n -Ci-C3-alkyl, where R b is as defined above and in particular selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C 2 -C6-alkenyl, C 2 -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 preferably selected from the group consisting of
  • variable R in the compounds of formula I is R b -S(0) n -Ci-C3-alkyl, where R b is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C7-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.
  • variable R in the compounds of formula I is R b -S(0) n -Ci-C2-alkyl, where R b is selected from Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • variable R in the compounds of formula I is R b -S(0) 2 -Ci-C 2 -alkyl, where R b is CH 3 , CH 2 H 3 , CH(CH 3 ) 2 ,
  • CH2CH2CH3, CH 2 CH CH 2 , CH 2 C ⁇ CH or phenyl.
  • variable R in the compounds of formula I is selected from the group consisting of methyl, ethyl, isopropyl, tert- butyl, cyclopropyl, cyclopentyl, cyclohexyl, CF 3 , CHF 2 , CCIF 2 , CH2CF3, CF2CF3, CH 2 CI, CHC , methoxyethyl, methoxymethyl, and in particular from methyl and ethyl.
  • Preferred compounds according to the invention are compounds of formula I , wherein R 5 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C5- cycloalkyl, C3-C5-cycloalkyl-Ci-C4-alkyl, where the C3-Cs-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C4-haloalkyl, C1-C3- alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-C4-alkoxy, Ci- C4-a I koxy-C 1 -C4-a I ky I , C 1 -C4-a I koxy-C 1 -C4-a I koxy-C 1 -C4-a I ky I
  • R 5 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci- C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-a I koxy-C 1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci- C4-alkylsulfonyl; specifically R 5
  • a particular group of compounds according to the invention are compounds of formula I, wherein X 1 is CR 1 .
  • R 1 is preferably selected from cyano, halogen, nitro, Ci-C6-alkyl, 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- haloal
  • R 1 is selected from cyano, nitro, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
  • R 1 is selected from the group consisting of cyano, nitro, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsufonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsufonyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl.
  • R 1 may also be selected from the group consisting of nitro, cyano, Ci-C4-alkoxy-Ci-C4-alkoxy and Ci-C4-haloalkoxy-Ci-C4-alkyl.
  • R 1 is F, CI, Br, N0 2 , CH 3 , CF 3 , OCH 3 , SCH 3 , OCF 3 , SCF 3 , SO2CH3,
  • variable R 1 in the compounds of formula I is selected from halogen, nitro, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl and C1-C4- alkylsufonyl.
  • examples are chlorine, fluorine, bromine, nitro, cyano, methyl, trifluoromethyl and methylsulfonyl.
  • R 1 is preferably selected from phe- noxy-Z 1 and heterocyclyloxy-Z 1 , where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heter- ocycle, 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 R 11 , which are identical or different.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-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-alkylsufonyl, in particular from F, CI, Br, nitro, CH 3 , CF 3 , OCH3, SCHs, OCF3, SCFs, SO2CH3, CH2OCH3 and CH2OCH2CH2OCH3; and
  • R 3 is is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci- C 4 -alkylsufonyl, in particular from H, CI, Br, CN, N0 2 , CH 3 , CF 3 , CHF 2 , OCH 3 , OCF 3 ,
  • a further embodiment of the invention relates to compounds of formula I, to their N-oxides and their salts, wherein X 1 is N.
  • a further embodiment of the invention relates to compounds of formula I, to their N-oxides and their salts, wherein X 2 is CR 2 .
  • Preferred compounds according to the invention are compounds of formula I, wherein R 2 has any one of the meanings given above for R 2 with the exception of hydrogen.
  • Particular embodiments of the invention relate to compounds of formula I, wherein X 2 is CR 2 and wherein the variable R 2 is heterocyclyl-Z 2a , where Z 2a is as defined herein and 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 the cyclic groups in heterocyclyl-Z 2a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R 21 , which are identical or different.
  • variable R 2 is preferably 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 or 2 further nitrogen atoms, where heterocyclyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 which are identical or different.
  • R 21 is preferably selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio and Ci-C4-alkylthio-Ci-C4-alkyl.
  • R 21 is selected from fluorine, chlorine methyl, ethyl, methoxy, ethoxy, methylsulfanyl, methylsulfonyl, methox- ymethyl, ethoxymethyl, ethylsulfanylmethyl, ethylsulfanylethyl, methylsulfanylmethyl, methyl- sulfanylethyl, fluoromethyl, difluoromethyl and trifluoromethyl.
  • X 2 is CR 2 and the variable R 2 is a 5- or 6-membered heterocyclyl selected from the group consisting of selected from the group consisting of isoxazolinyl, 1 ,2-dihydrotetrazolonyl, 1 ,4-dihydrotetrazolonyl, tetrahydro- furyl, dioxolanyl, piperidinyl, morpholinyl, piperazinyl, isoxazolyl, pyrazolyl, thiazolyl, oxazolyl, furyl, pyridinyl and pyrazinyl, where heterocyclyl is unsubstituted or carries 1 , 2 or 3 radicals R 21 , which are identical or different and selected from the group consisting of Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C
  • R 2 Especially preferred meanings for R 2 are 4,5-dihydroisoxazol-3-yl, 5-methyl-4,5-dihydroisoxazol-3-yl, 5- fluoromethyl-4,5-dihydroisoxazol-3-yl, 5-difluoromethyl-4,5-dihydroisoxazol-3-yl, 4,5- dihydroisoxazol-5-yl,3-methyl-4,5-dihydroisoxazol-5-yl, 3-methoxy-4,5-dihydroisoxazol-5-yl, 3- methoxymethyl-4,5-dihydroisoxazol-5-yl, 3-methylsulfanylmethyl, 4,5-dihydroisoxazol-5-yl, 1- methyl-5-oxo-1 ,5-dihydrotetrazol-2-yl; 4-methyl-5-oxo-4,5-dihydrotetrazol-1 -yl, morpholin-4-y
  • variable R 2 may also be 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.
  • Z 2a is a covalent bond.
  • Z 2a is Ci-C4-alkanediyl-0, such as OCH2 or OCH2CH2.
  • Z 2a is 0-Ci-C4-alkanediyl such as CH2O or CH2CH2O.
  • Z 2a is C1-C4- alkanediyl-0-CrC 4 -alkanediyl.
  • R 21 is preferably 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-C4-alkyl, Ci-C4-alkoxy, Ci-C2-haloalkyl and Ci-C4-alkoxy-Ci-C4- alkoxy such as fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, OCH2OCH3,
  • phenyl is unsubstituted or carries 1 radical R 21 .
  • variable R 2 in the compounds of formula I may be a radical of the following formula: in which # denotes the bond through which the group R 2 is attached and:
  • R P1 is hydrogen or halogen, preferably H, CI, Br or F, and in particular H or F;
  • R P2 is hydrogen, halogen or Ci-C2-alkoxy, preferably H, CI, Br, F, OCH3 or OCH2CH3, and in particular H, F, CI or OCH3; and
  • R P3 is hydrogen, halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-alkoxy-Ci-C2- alkoxy, preferably H, CI, Br, F, CH 3 , C 2 H 5 , CF 3 , CHF 2 , CH 2 F, CCI2F, CF 2 CI, CH2CF3, CH2CHF2, CF2CF3, OCH3, OCH2CH3, OCH2OCH3, OCH2CH2OCH2CH3, OCH2OCH2CH3 or
  • variable R 2 in the compounds of formula I is phenyl which is unsubstituted or carries one radical R 21 , where R 21 is attached to position 4 of the phenyl group and is selected from halogen Ci-C2-alkyl, Ci-C4-alkoxy, C1-C2- haloalkyl and Ci-C2-alkoxy-Ci-C2-alkoxy, preferably form fluorine, chlorine, bromine, CH3, C2H5, OCH3, OC2H5, CHF2, CF 3 , OCH2OCH3 and OCH2CH2OCH3, and specifically from OCH 3 and OC 2 H 5 .
  • variable R 2 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, C2-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6- haloalkenyloxy, C3-C6-haloalkynyloxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylsulfonyl, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfanyl and Ci-C4-
  • OCH 2 CH CH 2 , OCH 2 C ⁇ CH, C(0)OCH 3 , C(0)OC 2 H 5 , SO2CH3, S0 2 C 2 H 5 , S0 2 CH(CH 3 ) 2 , SOCH3, SOC 2 H 5 , SOCH(CH 3 ) 2 , SCH 3 , SC 2 H 5 and SCH(CH 3 ) 2 .
  • X is C-R 2 , wherein R 2 together with R 3 , if present, or together with R 1 , if present, forms a fused 5-, 6-, 7-, 8-, 9- or 10-membered carbocycle or a fused 5-, 6-, 7-, 8-, 9- or 10-membered heterocycle, where the fused heterocycle has 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members, where the fused carbocycle and the fused heterocycle are monocyclic or bicyclic and where the fused carbocycle and the fused heterocycle are unsubstituted or carry 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10 radicals R ⁇ .
  • X is C-R 2 , wherein R 2 together with
  • R 3 if present, or together with R 1 , if present, forms a fused 5-, 6-, 7-, 8-, 9- or 10-membered carbocycle or a fused 5-, 6-, 7-, 8-, 9- or 10-membered heterocycle, where the fused
  • heterocycle has 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members, where the fused carbocycle and the fused heterocycle are monocyclic or bicyclic and where the fused carbocycle and the fused heterocycle are unsubstituted or carry 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10 radicals R ⁇ .
  • the ring member S can optionally be oxidized to various oxidation states.
  • the ring member N can optionally be oxidized. Together with the six-membered N-heteroaromatic group to which they are attached a nine- to fifteen-membered bi- or tricyclic ring system results.
  • the heteroaromatic group is preferably fused to a benzene, naphthaline, C5-C10- cycloalkane, or heterocyclic ring having 5 to 10 ring members.
  • a ring system where R 2 together with R 3 or together with R 1 forms a fused 5-, 6-, 7-, 8-, 9- or 10-membered carbocycle or a fused 5-, 6-, 7-, 8-, 9- or 10-membered heterocycle as defined above are quinoline, isoquinoline, quinoxaline, benzo[g]isoquinoline, 5,6,7,8,-tetrahydroisoquinoline, 5,8- dihydroisoquinoline, 1 ,5-naphthyridine, 1 ,6-naphthyridine, 2,6-naphthyridine, 1 ,7-naphthyridine, 2,7-naphthyridine, 1 ,8-naphth
  • Examples are the groups A.1 , A.2, A.3, A.4 and A.5:
  • A.1 A.2 A.3 A.4 A.5 # denotes the bond to the carbonyl carbon atom of N-(tetrazol-5-yl)- or N-(triazol-5- yl)aminocarbonyl group;
  • X 1 , X 4 , R 5 and R ⁇ are as defined above.
  • A.6 A.7 A.8 A.9 A.10 # denotes the bond to the carbon atom of the carbonyl group of the N-(tetrazol-5-yl)- or N- (triazol-5-yl)aminocarbonyl group;
  • X 4 is N and R 3 , R 5 and R ⁇ are as defined above;
  • X 2 is N.
  • a further embodiment of the invention relates to compounds of formula I, to their N-oxides and their salts, wherein X 3 is CR 3 .
  • Preferred compounds according to the invention are compounds of formula I, wherein R 3 has any one of the meanings given above for R 3 with the exception of hydrogen.
  • Particular embodiments of the invention relate to compounds of formula I, wherein X 3 is CR 3 and wherein the variable R 3 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2- C4-alkynyl, C2-C4-alkenyloxy, C2-C4-alkynyloxy and R 2b -S(0)k.
  • the variable R 3 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2- C4-alkynyl, C2-C4-alkenyloxy, C2-C4-alkynyloxy and
  • Particular preferred embodiments of the invention relate to compounds of formula I, wherein X 3 is CR 3 and wherein the variable R 3 is selected from the group consisting of hydrogen, halogen, CN, N0 2 , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, C1-C4- haloalkylthio, Ci-C 4 -alkyl-S(0) 2 and Ci-C 4 -haloalkyl-S(0) 2 .
  • the variable R 3 is selected from the group consisting of hydrogen, halogen, CN, N0 2 , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, C1-C4- haloalkylthio, Ci
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-
  • variable R 3 in the compounds of formula I is selected from hydrogen, cyano, halogen, Ci-C 4 -haloalkyl and Ci-C 4 -alkylsulfonyl, such as hydrogen, cyano, chlorine, trifluoromethyl, difluoromethyl, S(0)2CH3 and S(0)2CH2CH3.
  • R 3 in the compounds of formula I is selected from hydrogen, chlorine, fluorine, trifluoromethyl, methylsulfonyl and cyano.
  • X 3 is N.
  • X 4 is CR 4 .
  • R 4 is preferably selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C 4 -alkyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C 4 -alkyl, where the C3-C5- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C 4 -haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 --alkoxy-Ci-C 4 -
  • R 4 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci- C 4 -alkyl, C3-C 4 -cycloalkyl, C3-C 4 -cycloalkyl-Ci-C2-alkyl, where the C3-C 4 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 - alkoxy-Ci-C 4 -alkyl, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkylsulfinyl, Ci- C 4 -al
  • R', R 11 , R 21 independently of each other are selected from halogen, Ci-C4-alkyl, C1-C4- haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy and Ci-C4-haloalkyloxy, more preferably from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, and in particular from CI, F, Br, methyl, ethyl, methoxy and trifluoromethyl.
  • Z, Z 1 , Z 2 independently of each other are selected from covalent bond methanediyl and ethanediyl.
  • 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 hetero- cyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • R c , R 2c and R k independently of each other are selected from hydrogen, Ci-C6-alkyl, Ci- C6-haloalkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, 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 consist
  • 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 Ci-C4-alkyl, C1-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, Ci-C6-haloalkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, 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, C2-C4- haloalkynyl 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, Ci-C6-haloalkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, 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 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, C1-C6- haloalkyi, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl,C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl; more preferably Rs, R3 ⁇ 4 independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-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
  • 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; more preferably Rs and R h or R3 ⁇ 4 and R 2h together with the nitrogen atom, to which they are bound 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 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 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 is preferably are 0.
  • k is preferably 0 or 2.
  • Specially preferred are compounds of formula I, wherein two of X 1 , X 2 , X 3 and X 4 are N.
  • a particularly preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is N, X 2 is CR 2 , X 3 is CR 3 and X 4 is CR 4 .
  • These compounds are also referred to as compound of formula 1.1 , wherein R 2 , R 3 , R 4 , R 5 and R are as defined
  • R 2 , R 3 , R 4 , R 5 and R have the preferred meanings mentioned above.
  • R 3 , R 4 , R 5 and R have the preferred meanings mentioned above and the variable R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C2- haloalkoxy-Ci-C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl.
  • R 2 is selected from hydrogen, methoxymethyl, ethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, methylsulfonyl, methylsulfinyl, methylsulfanyl, 4,5-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 3-methyl-4,5-dihydroisoxazol-5-yl, 5-methyl-4,5-dihydroisoxazol-3-yl, isoxazol-5-yl, 3-methyl- isoxazol-5-yl, isoxazol-3-yl and 5-methyl-isoxazol-3-yl.
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C2- haloalkoxy-Ci-C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl , isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl, in particular hydrogen, methoxymethyl, ethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, methylsulfonyl, methylsulfinyl , methylsulfanyl, 4,5-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 3- methyl-4,5-d
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl, in particular H, CI, F, CF 3 , SO2CH3 or CN;
  • R 4 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl; and R 5 is
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C2- haloalkoxy-Ci-C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be 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, NO2, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl;
  • R 4 is H; and R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl,
  • R 5 is H; and R 4 is selected from the group consisting of cyclopropyl, cyclopropylmethyl,
  • Table 1 Compounds of formula 1.1 (compounds 1.1 -1 to 1.1-336) in which B is CH and R 2 is hydrogen and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 4 Compounds of formula 1.1 (compounds 1.1 -1009 to 1.1 -1344), in which B is CH and R 2 is SO2CH3 and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 5 Compounds of formula 1.1 (compounds 1.1 -1345 to 1.1 -1680) in which B is CH and
  • R 2 is 2,2,2-trifluoroethoxymethyl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • R 2 is 5-methyl-4,5-dihydroisoxazol-3-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • R 2 is 4,5-dihydroisoxazol-5-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • R 2 is 3-methyl-4,5-dihydroisoxazol-5-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • R 2 is isoxazol-3-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 1 Compounds of formula 1.1 (compounds 1.1 -3361 to 1.1 -3696) in which B is CH and R 2 is 5-methyl-isoxazol-3-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • R 2 is isoxazol-5-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • R 2 is 3-methyl-isoxazol-5-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 14 Compounds of formula 1.1 (compounds 1.1 -4369 to 1.1 -4704) in which B is N and R 2 is hydrogen and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 15 Compounds of formula 1.1 (compounds 1.1 -4705 to 1.1 -5040) in which B is N and R 2 is SCH3 and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 17 Compounds of formula 1.1 (compounds 1.1 -5377 to 1.1 -5712), in which B is N and R 2 is SO2CH3 and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 18 Compounds of formula 1.1 (compounds 1.1 -5713 to 1.1 -6048) in which B is N and R 2 is 2,2,2-trifluoroethoxymethyl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 25 Compounds of formula 1.1 (compounds 1.1 -8065 to 1.1 -8400) in which B is N and R 2 is isoxazol-5-yl and the combination of R, R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table A;
  • a further particularly preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is N, X 2 is N, X 3 is CR 3 and X 4 is CR 4 .
  • These compounds are also referred to as compound of formula 1.3, wherein R 3 , R 4 , R 5 and R are as defined hereinabove for compounds of formula I:
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl, in particular H, F, CI, Br, CN, N0 2 , CH 3 , CH 2 CH 3 , CF 3 , CHF 2 , OCH 3 , OCF 3 , OCHF 2 , S0 2 CH 3 or S0 2 CH 2 CH 3 ;
  • R 4 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl; and
  • R 5 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl; provided that if
  • R is Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C 4 -alkyl, C1-C4- haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -haloalkylthio and Ci-C 4 -alkylsufonyl;
  • R 4 is H; and
  • R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl,
  • R 5 is H; and R 4 is selected from the group consisting of cyclopropyl, cyclopropylmethyl,
  • a further particularly preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is C-R 1 , X 3 is C-R 3 , X 2 is N and X 4 is N.
  • This compound is also referred to as compound of formula 1.4, wherein R 1 , R 3 , R 5 and R are as defined hereinabove for compounds of formula I:
  • R 3 , R 5 and R have the preferred meanings and the variable R 1 is selected from the group consisting of halogen, nitro, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio and Ci-C 4 -alkylsulfonyl, in particular from F, CI, Br, nitro, CH 3 , CF 3 , OCH 3 , OCF 3 , OCHF 2 , SCF 3 , SCHF 2 , S0 2 CH 3 and
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, C1-C4- haloalkylthio or Ci-C4-alkylsulfonyl, in particular F, CI, Br, I, nitro, CH3, CF3, OCH3, OCF3,
  • R 3 is hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl, in particular H, F, CI, Br, CN, NO2, CH 3 , CH2CH3, CF 3 , CHF 2 , OCH3, OCF3, OCHF2, SCH 3 , SO2CH3 or SO2CH2CH3; and R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl, OCH3, OCH2CH3, OCH(CH 3 ) 2 , CH2OCH3, CH2OCH2CH2OCH3, OCF3, OCHF2, SCH 3 , SCF 3 , SCH2CH3, SCH2CF3, SOCH3, SOCH2CH3, SO2CH3, SO2CH2,CH3.
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is 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 or Ci-C4-alkylsulfonyl;
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl; and R 5 is selected from the group consisting of cyclopropyl, OCH3, OCF3, SCH3, SOCH3, SO2CH3 or CH 2 OCH 3 .
  • Table 30 Compounds of formula I.4 (compounds 1.4-505 to 1.4-672) in which B is CH and R 1 is trifluoromethyl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 31 Compounds of formula 1.4 (compounds I.4-673 to I.4-840) in which B is CH and R 1 is methylsulfonyl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa.
  • Table 36 Compounds of formula I.4 (compounds 1.4-1513 to 1.4-1680) in which B is N and R 1 is methylsulfonyl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa.
  • Table Aa
  • a further particularly preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is C-R 1 , X 2 is C-R 2 , X 3 is C-R 3 and X 4 is N.
  • This compound is also referred to as compound of formula 1.5, wherein R 1 , R 2 , R 3 , R 5 and R are as defined
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is 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 or Ci-C 4 -alkylsulfonyl, in particular F, CI, Br, I, nitro, CH 3 , CF 3 , OCH 3 , OCF 3 , OCHF 2 ,
  • R 2 is hydrogen, Ci-C 2 -alkoxy-Ci-C 2 -alkyl, Ci-C 2 -haloalkoxy-Ci-C 2 -alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl, in particular
  • R 3 is H, halogen, CN, N0 2 , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkylthio, C1-C4- haloalkylthio or Ci-C 4 -alkylsulfonyl, in particular H, F, CI, Br, CN, N0 2 , CH 3 , CH 2 CH 3 , CF 3 , CHF 2 , OCH 3 , OCF 3 , OCHF 2 , SCH 3 , S0 2 CH 3 or S0 2 CH 2 CH 3 ; and
  • R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl, OCH 3 , OCH 2 CH 3 , OCH(CH 3 ) 2 , CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , OCF 3 , OCHF 2 , SCH 3 , SCF 3 , SCH 2 CH 3 ,
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-
  • R 2 is selected from the group consisting of hydrogen, Ci-C 2 -alkoxy-Ci-C 2 -alkyl, Ci-C 2 - haloalkoxy-Ci-C 2 -alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be 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, N0 2 , Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl; and R 5 is selected from the group consisting of cyclopropyl, OCH 3 , OCF 3 , SCH 3 , SOCH 3 , S0 2 CH 3 or CH 2 OCH 3 .
  • R 2 is hydrogen and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is SOCH3 and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is SO2CH3 and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 2,2,2-trifluoroethoxymethyl and the combination of R, R 1 , R 3 and R 5 for a com- pound corresponds in each case to one row of Table Ab;
  • R 2 is 4,5-dihydroisoxazol-3-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 4,5-dihydroisoxazol-5-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 3-methyl-4,5-dihydroisoxazol-5-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is isoxazol-3-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 5-methyl-isoxazol-3-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is hydrogen and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • Table 50 Compounds of formula 1.5 (compounds 1.5-10921 to 1.5-1 1760), in which B is N and
  • R 2 is SCH3 and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is SO2CH3 and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 2,2,2-trifluoroethoxymethyl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 4,5-dihydroisoxazol-3-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 5-methyl-4,5-dihydroisoxazol-3-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 3-methyl-4,5-dihydroisoxazol-5-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is isoxazol-3-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 5-methyl-isoxazol-3-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab;
  • R 2 is 3-methyl-isoxazol-5-yl and the combination of R, R 1 , R 3 and R 5 for a compound corresponds in each case to one row of Table Ab.
  • a further very preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is N, X 4 is N, X 2 is CR 2 and X 3 is CR 3 .
  • These compounds are also referred to as compound of formula 1.6, wherein R 2 , R 3 , R 5 and R are as defined hereinabove for compounds of formula I:
  • R 2 , R 3 , R 5 and R have the preferred meanings mentioned above.
  • R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy-Ci- C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl.
  • R 2 is selected from hydrogen, methoxymethyl, ethoxyme- thyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, methylsulfonyl, methylsulfinyl, me- thylsulfanyl, 4,5-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 3-methyl-4,5-dihydroisoxazol-5- yl, 5-methyl-4,5-dihydroisoxazol-3-yl, isoxazol-5-yl, 3-methyl-isoxazol-5-yl, isoxazol-3-yl and 5- methyl-isoxazol-3-yl.
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C2- haloalkoxy-Ci-C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl, in particular hydrogen, methoxymethyl, ethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, methylsulfonyl, methylsulfinyl, methylsulfanyl, 4,5-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 3-methyl- 4,5-
  • R 3 is selected from the group consisting of hydrogen, halogen, CN, NO2, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl, in particular H, CI, F, CF 3 , SO2CH3 or CN; and
  • R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl, OCH3, OCH2CH3, OCH(CH 3 ) 2 , CH2OCH3, CH2OCH2CH2OCH3, OCF3, OCHF2, SCH 3 , SCF 3 , SCH2CH3,
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C2- haloalkoxy-Ci-C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl,, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be 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, NO2, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-haloalkylthio and Ci-C4-alkylsufonyl; and
  • R 5 is selected from the group consisting of cyclopropyl, OCH3, OCF3, SCH3, SOCH3, SO2CH3 or CH 2 OCH 3 .
  • Table 65 Compounds of formula 1.6 (compounds 1.6-673 to 1.6-840) in which B is CH and R 2 is 2,2,2-trifluoroethoxymethyl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 68 Compounds of formula 1.6 (compounds 1.6-1 177 to 1.6-1344) in which B is CH and R 2 is 4,5-dihydroisoxazol-5-yl and the combination of R, R 3 and R 5 for a compound cor- responds in each case to one row of Table Aa;
  • Table 69 Compounds of formula 1.6 (compounds 1.6-1345 to 1.6-1512) in which B is CH and R 2 is 3-methyl-4,5-dihydroisoxazol-5-yl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 70 Compounds of formula 1.6 (compounds 1.6-1513 to 1.6-1680) in which B is CH and R 2 is isoxazol-3-yl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 72 Compounds of formula 1.6 (compounds 1.6-1849 to 1.6-2016) in which B is CH and R 2 is 3-methyl-isoxazol-5-yl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 74 Compounds of formula I.6 (compounds 1.6-2185 to 1.6-2352), in which B is N and R 2 is SCH3 and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 75 Compounds of formula 1.6 (compounds 1.6-2353 to 1.6-2520), in which B is N and R 2 is SOCH3 and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 80 Compounds of formula 1.6 (compounds 1.6-3193 to 1.6-3360) in which B is N and R 2 is 4,5-dihydroisoxazol-5-yl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 81 Compounds of formula 1.6 (compounds 1.6-3361 to 1.6-3528) in which B is N and R 2 is 3-methyl-4,5-dihydroisoxazol-5-yl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 82 Compounds of formula 1.6 (compounds 1.6-3529 to 1.6-3696) in which B is N and R 2 is isoxazol-3-yl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • Table 84 Compounds of formula 1.6 (compounds 1.6-3865 to 1.6-4032) in which B is N and R 2 is 3-methyl-isoxazol-5-yl and the combination of R, R 3 and R 5 for a compound corresponds in each case to one row of Table Aa;
  • a further particularly preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is C-R 1 , X 2 is CR 2 , X 3 is CR 3 , X 4 is N and R 2 together with R 3 forms a fused 6-membered carbocycle.
  • This compound is also referred to as compound of formula 1.7, wherein R 1 , R 5 and R are as defined hereinabove for compounds of formula I:
  • R 5 and R have the preferred meanings and the variable R 1 is selected from the group consisting of halogen, nitro, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio and Ci-C 4 -alkylsulfonyl, in particular from F, CI, Br, nitro, CH 3 , CF 3 , OCH 3 , OCF 3 , OCHF 2 , SCF 3 , SCHF 2 , S0 2 CH 3 and CH 2 OCH 2 CH 2 OCH 3 .
  • R is Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is halogen, nitro, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 - alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkylthio, Ci-C 4 - haloalkylthio or Ci-C 4 -alkylsulfonyl, in particular F, CI, Br, I, nitro, CH 3 , CF 3 , OCH 3 , OCF 3 ,
  • R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl, OCH 3 , OCH 2 CH 3 , OCH(CH 3 ) 2 , CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , OCF 3 , OCHF 2 , SCH 3 , SCF 3 , SCH 2 CH 3 , SCH 2 CF 3 , SOCHs, SOCH 2 CH 3 , S0 2 CH 3 , S0 2 CH 2 CH 3 .
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is 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 or Ci-C4-alkylsulfonyl; and
  • R 5 is selected from the group consisting of cyclopropyl, OCH3, OCF3, SCH3, SOCH3, SO2CH3 or CH 2 OCH 3 .
  • Table 90 Compounds of formula 1.7 (compounds 1.7-101 to 1.7-120), in which B is CH and R 5 is SO2CH3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac.
  • Table 94 Compounds of formula 1.7 (compounds 1.7-181 to 1.7-200), in which B is N and R 5 is OCF3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac.
  • Table 95 Compounds of formula 1.7 (compounds 1.7-201 to 1.7-220) in which B is N and R 5 is SCH3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac;
  • a further particularly preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is C-R 1 , X 2 is CR 2 , X 3 is CR 3 , X 4 is N and R 2 together with R 3 forms a fused 6-membered heterocycle, where the fused heterocycle has 1 nitrogen atom as ring member.
  • This compound is also referred to as compound of formula 1.8, wherein R 1 , R 5 and R are as defined hereinabove for compounds of formula I:
  • R 5 and R have the preferred meanings and the variable 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, nitro, CH 3 , CF 3 , OCH 3 , OCF 3 , OCHF 2 , SCF 3 , SCHF 2 , S0 2 CH 3 and CH 2 OCH 2 CH 2 OCH 3 .
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- a I koxy-C 1 -C4-a I ky I , C 1 -C4-a I koxy-C 1 -C4-a I koxy-C 1 -C4-a I ky I , C 1 -C4-a I ky I th i o , C 1 -C4- haloalkylthio or Ci-C4-alkylsulfonyl, in particular F, CI, Br, I, nitro, CH 3 , CF 3 , OCH 3 , OCF 3 , OCHF 2 , CH 2 OCH 2 CH 2 OCH 3 , SCF 3 , SCHF 2 or S0 2 CH 3 ; and
  • R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl, OCH 3 , OCH 2 CH 3 , OCH(CH 3 ) 2 , CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , OCF 3 , OCHF 2 , SCH 3 , SCF 3 , SCH 2 CH 3 , SCH 2 CF 3 , SOCHs, SOCH 2 CH 3 , S0 2 CH 3 , S0 2 CH 2 CH 3 .
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-a I koxy-C 1 - C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio or Ci-C4-alkylsulfonyl; and
  • R 5 is selected from the group consisting of cyclopropyl, OCH 3 , OCF 3 , SCH 3 , SOCH 3 , S0 2 CH 3 or CH 2 OCH 3 .
  • Table 102 Compounds of formula 1.8 (compounds 1.8-61 to 1.8-80) in which B is CH and R 5 is SCH 3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac;
  • Table 103 Compounds of formula 1.8 (compounds 1.8-81 to 1.8-100), in which B is CH and R 5 is SOCH3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac;
  • Table 104 Compounds of formula I.8 (compounds 1.8-101 to 1.8-120), in which B is CH and R 5 is SO2CH3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac.
  • Table 1 10 Compounds of formula 1.8 (compounds 1.8-221 to 1.8-240), in which B is N and R 5 is SOCH3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac;
  • Table 1 1 1 Compounds of formula I.8 (compounds 1.8-241 to 1.8-260), in which B is N and R 5 is SO2CH3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac.
  • Table 1 12 Compounds of formula 1.8 (compounds 1.8-261 to 1.8-280), in which B is N and R 5 is CH2OCH3 and the combination of R and R 1 for a compound corresponds in each case to one row of Table Ac.
  • a further very preferred embodiment of the present invention relates to compounds of formula I, wherein X 1 is N, X 3 is N, X 2 is CR 2 and X 4 is CR 4 .
  • These compounds are also referred to as compound of formula 1.9, wherein R 2 , R 4 , R 5 and R are as defined hereinabove for compounds of formula I:
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C2- haloalkoxy-Ci-C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl, in particular hydrogen, methoxymethyl, ethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, methylsulfonyl, methylsulfinyl, methylsulfanyl, 4,5-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 3-methyl-
  • R 4 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, d-Cs alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl; and
  • R 5 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl; provided that if
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 2 is selected from the group consisting of hydrogen, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C2- haloalkoxy-Ci-C2-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfanyl, isoxa- zolyl and isoxazolinyl, where the last two mentioned radicals may be substituted or carry 1 or 2 radicals selected from halogen and Ci-C4-alkyl;
  • R 4 is H; and R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl,
  • R 5 is H; and R 4 is selected from the group consisting of cyclopropyl, cyclopropylmethyl,
  • a further very preferred embodiment of the present invention relates to compounds of formula I , wherein X 1 is CR 1 , X 2 is N, X 3 is N and X 4 is CR 4 . These compounds are also referred to as compound of formula 1.10, wherein R 1 , R 4 , R 5 and R are as defined hereinabove for compounds of formula I:
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, C1-C4- haloalkylthio or Ci-C4-alkylsulfonyl, in particular F, CI, Br, I, nitro, CH3, CF3, OCH3, OCF3, OCHF2, CH2OCH2CH2OCH3, SCF 3 , SCHF 2 or SO2CH3;
  • R 4 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl; and
  • R 5 is selected from the group consisting of hydrogen, halogen, CN, nitro, Ci-C4-alkyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, where the C3-C4-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- haloalkyl, Ci-C3 alkylcarbonyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl; provided that if
  • R is Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, in particular methyl, ethyl, methoxymethyl and methoxyethyl;
  • R 1 is 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 or Ci-C4-alkylsulfonyl;
  • R 4 is H; and R 5 is selected from the group consisting of cyclopropyl, cyclopropylmethyl, OCHs, OCH2CH3, OCH(CH 3 ) 2 , CH2OCH3, CH2OCH2CH2OCH3, OCF3, OCHF2, SCH 3 , SCF 3 , SCH2CH3, SCH2CF3, SOCH3, SOCH2CH3, SO2CH3, SO2CH2CH3; or
  • R 5 is H; and R 4 is selected from the group consisting of cyclopropyl, cyclopropylmethyl, OCH3, OCH2CH3, OCH(CH 3 ) 2 , CH2OCH3, CH2OCH2CH2OCH3, OCF3, OCHF2, SCH 3 ,
  • 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 8.
  • the substituents, variables and indices in schemes 1 to 8 are as defined above for formula I, if not otherwise specified.
  • Y is a leaving group, such as halogen, in particular CI, an anhydride residue or an active ester residue.
  • 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 solvents 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 reacted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of -20°C
  • compounds of formula I can also be prepared as shown in Scheme 2.
  • Reaction of 5-amino-1 -R-1 ,2,4-triazole or 5-amino-1 -R-tetrazole of formula III with a benzoic acid derivative of formula IV yields compound I.
  • the reaction is preferably carried in the presence of a suitable activating agent, which converts the acid group of compound IV into an activated ester or amide.
  • activating agents known in the art, such as
  • 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
  • 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.
  • hydroxybenzotri- azole HOBt
  • nitrophenol pentafluorophenol
  • 2,4,5-trichlorophenol N-hydroxysuccinimide
  • N-hydroxysuccinimide N-hydroxysuccinimide
  • 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.
  • dichloromethane or dichloroethane ethers, e.g. tetrahydrofuran or 1 ,4-dioxane or carboxamides, e.g. N,N- dimethylformamide, ⁇ , ⁇ -dimethylacetamide or N-methylpyrrolidone.
  • ethers e.g. tetrahydrofuran or 1 ,4-dioxane
  • 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 obtained by purchase or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO 2000039094, WO 20091 15788 , EP 316491 and EP 283261 .
  • compounds of formula I can be obtained by treating N-(1 H-1 ,2,4-triazol-5- yl)benzamides or N-(1 H-tetrazol-5-yl)benzamides of formula V with, for example, alkylating agents such as alkyl halides according to Scheme 3.
  • 5-amino-1 -R-tetrazoles of formula III where R is for example alkyl, are either commercially available or are obtainable according to methods known from the literature.
  • 5-amino-1 -R-tetrazole can be prepared from 5-aminotetrazole according to the method described in the Journal of the American Chemical Society, 1954, 76, 923-924 (Scheme 4).
  • 5-amino-1 -R-triazoles of formula III are either commercially available or are obtainable according to methods described in the literature.
  • 5-amino-1 -R-triazole can be prepared from 5-aminotriazole according to the method described in Zeitschrift fur Chemie, 1990, 30, 12, 436-437.
  • 5-Amino-1 -R-triazole compounds of formula III can also be prepared analogous to the synthesis described in Chemische Berichte, 1964, 97, 2, 396-404, as shown in Scheme 7.
  • 5-amino-1 -R-triazoles of formula III can be prepared according to the synthesis described in Angewandte Chemie, 1963, 75, 918 (Scheme 8).
  • 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 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
  • 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 recrystallization or trituration.
  • the compounds 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 I in particular 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
  • HPPD hydroxyphenyl pyruvate dioxygenase
  • ALS acetolactate synthase
  • EP-A-0257993, US 5,013,659 sulfonylureas
  • imidazolinones see, for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526,
  • EPSPS enolpyruvylshikimate 3-phosphate synthase
  • EPSPS enolpyruvylshikimate 3-phosphate synthase
  • GS glutamine synthetase
  • glufosinate see, for example, EP-A-0242236, EP-A-242246, or oxynil herbicides (see, for example, US 5,559,024).
  • mutagenesis Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady ®
  • crop plants also includes plants which, with the aid of genetic engineering, 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 (VIPs), for example VIP1 , VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, for example Photorhabdus spp.
  • VIPs vegetative insecticidal proteins
  • toxins of animal organisms for example wasp, spider or scorpion toxins
  • fungal toxins for example from Streptomycetes
  • plant lectins for example from peas or barley
  • agglutinins proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribosome-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 wasp, spider or scorpion toxins
  • fungal toxins for example from Streptomycetes
  • these toxins may also be produced as pretoxins, 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.
  • 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 example by oil plants producing health-promoting long-chain omega 3 fatty acids or
  • monounsaturated 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. 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.
  • the compounds I, or the herbicidal compositions comprising the compounds 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.

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Abstract

L'invention concerne des N-(tétrazol-5-yl)- et N-(triazol-5-yl)hétarylcarboxamides représentés par la formule (I) et leur utilisation en tant qu'herbicides. L'invention concerne des N-(tétrazol-5-yl)- et N-(triazol-5-yl)hétarylcarboxamides de formule (I) et leur utilisation en tant qu'herbicides. Dans ladite formule (I), B représente N ou CH, alors que X1 représente N ou CR1, X2 représente N ou CR2, X3 représente N ou CR3 et X4 représente N ou CR4; pour autant qu'au moins l'un des éléments parmi X1, X3 et X4 représente N; R, R1, R2, R3, R4 et R5 représentent des groupes tels que hydrogène, halogène ou des groupes organiques tels qu'alkyle ou phényle.
PCT/EP2014/059378 2013-05-15 2014-05-07 Composés de n-(tétrazol-5-yl)- et n-(triazol-5-yl)hétarylcarboxamide substitués et leur utilisation en tant qu'herbicides Ceased WO2014184074A1 (fr)

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