WO2019162309A1 - Composés benzamide et leur utilisation en tant qu'herbicides - Google Patents

Composés benzamide et leur utilisation en tant qu'herbicides Download PDF

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WO2019162309A1
WO2019162309A1 PCT/EP2019/054181 EP2019054181W WO2019162309A1 WO 2019162309 A1 WO2019162309 A1 WO 2019162309A1 EP 2019054181 W EP2019054181 W EP 2019054181W WO 2019162309 A1 WO2019162309 A1 WO 2019162309A1
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alkyl
group
alkoxy
cycloalkyl
haloalkyl
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PCT/EP2019/054181
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English (en)
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Thomas Zierke
Markus Kordes
Thomas Seitz
Ryan Louis NIELSON
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • 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
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical

Definitions

  • the present invention relates to benzamide compounds carrying an alkoxy group on the phenyl ring which is in turn substituted by a group containing a specific amide group, the N- oxides and salts thereof and to compositions comprising the same.
  • the invention also relates to the use of said benzamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation, and to a method for controlling unwanted vegetation by applying said compounds or compositions.
  • WO 2013/174845 describe N-(tetrazol-5-yl)- and N-(triazol-5-yl)-benzamides carrying substitu- ents in the 2- and 4-positions and optionally also in the 3-position of the phenyl ring and their use as herbicides.
  • WO 2013/124245 moreover also relates to N-(1 ,3,4-oxadiazol-2-yl)-4- nitrobenzamides.
  • WO 2012/126932 relates to N-(1 ,3,4-oxadiazol-2-yl)-benzamides carrying substituents in the 2-, 3- and 4-positions.
  • WO 2011/035874 relates to N-(1 ,2,5-oxadiazol-3-yl)- benzamides carrying substituents in the 2-, 3- and 4-positions.
  • the substituent in the 3-position of the phenyl ring is inter alia defined as a group OR 1 , where R 1 is inter alia alkyl which may inter alia carry an amide group C(0)N(R 3 ) 2 , where R 3 is hydrogen, alkyl, alkenyl or alkynyl; in some of the above documents also cycloalkyl, cycloalkyl-alkyl or phenyl.
  • the compounds of the prior art often suffer from insufficient herbicidal activity in particular at low application rates and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.
  • benzamide corn- pounds having a strong herbicidal activity, in particular even at low application rates, a suffi- ciently low toxicity for humans and animals and/or a high compatibility with crop plants.
  • the benzamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.
  • Q is selected from the group consisting of radicals of the formulae Q 1 , Q 2 , Q 3 and Q 4 ;
  • R 1 is selected from the group consisting of cyano, halogen, nitro, C-i-Cs-alkyl, C-i-Cs-haloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- Cs-alkoxy, Ci-C 6 -haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Z 1 - and R 1 b -S(0) k -Z 1 -;
  • R 2 is a radical of the formula R.2;
  • # in formula R.2 indicates the point of attachment to the oxygen atom bearing R 2 ;
  • R 3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, nitro, hy- droxy-Z 3 -, Ci-C 6 -alkyl, C-i-Cs-haloalkyl, Ci-C4-cyanoalkyl, C2-Cs-alkenyl, C2-Cs-haloalkenyl, C2-Cs-alkynyl, C 3 -C 8 -haloalkynyl, C 3 -Cio-cycloalkyl-Z 3 -, C 3 -C 6 -cycloalkenyl-Z 3 -, C 3 -Cio- cycloalkoxy-Z 3 -, C 3 -Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four afore- mentioned radicals are unsubstituted or partially or completely halogenated; C-i-Cs-alkoxy- Z
  • R 4 is selected from the group consisting of hydrogen, halogen, cyano-Z 1 , nitro, C-i-Cs-alkyl, C-i-Cs-haloalkyl, 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 hal- ogenated; C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, Ci-C3-alkylamino, di-(Ci-C3-alkyl)-amino, C1-C3- aikylamino-S(0) k -, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, Ci-C 6 -haloalkoxy, Ci-C 4 -alkoxy-C-i- C 4 -al
  • R 2a is Ci-C 6 -haloalkyl
  • R 2b is selected from the group consisting of hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C1-C6- cyanoalkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C 4 -alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely hal ogenated; Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - alkynyl, C3-C6-haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkyl-S(0) n -Ci-C 4 -alkyl, Ci-C 4 -
  • R b , R 1b and R 3b are selected from the group consisting of C 1 -C 6 - alkyl, Ci-C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle containing 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S as ring members, 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, Ci-C 4 -alkyl, C 1 -C 4 - hal
  • R 3c is selected from the group consisting of hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 1 -C 6 - cyanoalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely hal- ogenated; C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 - alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkyl-S(0) n -Ci-C 4 -alkyl, Ci-C 4
  • R 3d is selected from the group consisting of hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 1 -C 6 - cyanoalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely hal- ogenated; C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 - alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkyl-S(0) n -Ci-C 4 -alkyl, Ci-C 4
  • R 3e , R 3f independently of each other, are selected from the group consisting of hydrogen, C 1 - C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 - cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or com- pletely halogenated, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical
  • R3 ⁇ 4 is selected from the group consisting of hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 7 - cycloalkyl, C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C 2 -C 6 - alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 1 - C 4 -alkylsulfonyl, Ci-C 4 -alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are un- substituted or substituted
  • R 3h is selected from the group consisting of hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 7 - cycloalkyl, C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C 2 -C 6 - alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 1 - C 4 -alkylsulfonyl, Ci-C 4 -alkylcarbonyl, a radical C(0)R k , phenyl and benzyl, where phenyl and benzy
  • R 1 1 and R 21 are selected from the group consisting of cyano, halo- gen, nitro, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 6 -alkoxy, C 1 -C 6 - haloalkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, Ci-C4-alkylthio-Ci-C4- alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4
  • R 23 is selected from the group consisting of hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl and phenyl;
  • R 24 is selected from the group consisting of Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl and phenyl;
  • R 25 is selected from the group consisting of Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, C3-C6-cycloalkyl-Ci- C 6 -alkoxy-Ci-C 6 -alkyl, phenyl-Z 1 , phenyl-0-Ci-C 6 -alkyl, phenyl-N(R 23 )-Ci-C 6 -alkyl, phenyl- S(0)
  • Z 1 , Z 3 independently of each other, are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl which is unsubstituted or is partly or completely fluorinated;
  • Z 2 is a covalent bond or linear Ci-C4-alkanediyl
  • Ci-C4-alkanediyl group is unsubstituted or partly or completely fluorinated or substituted by 1 , 2, 3 or 4 groups R z , Z 3a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-C1-C4- alkanediyl, Ci-C 4 -alkanediyl-0 and Ci-C 4 -alkanediyl-0-Ci-C 4 -alkanediyl; each R z is independently selected from the group consisting of Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C1- C 6 -cyanoalkyl, 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 radicals
  • R k independently has one of the meanings given for R 3c ; k is 0, 1 or 2; and n is 0, 1 or 2; or an N-oxide or an agriculturally suitable salt thereof.
  • the invention also relates to a composition comprising a compound of formula I, an N- oxide or a salt thereof, and at least one auxiliary.
  • the invention relates to an agri- cultural composition comprising a compound of formula I or an N-oxide or an agriculturally suit- able salt thereof, and at least one auxiliary customary for crop protection formulations.
  • the composition of the invention may of course also contain more than one compound I; e.g. 2 or 3 different compounds I.
  • the composition may also contain a mixture of a compound I and an N- oxide thereof or of a compound I and a salt thereof or of a compound I, and N-oxide and a salt thereof.
  • Such mixtures of a compound I, and N-oxide and/or a salt thereof can for example re- suit if the conversion of the compound I into its N-oxide or its salt is not complete and the sepa- ration of the mixture is not deemed necessary.
  • the compounds of the present invention i.e. the compounds of formula I, their N-oxides and their agriculturally suitable salts, are particularly useful for controlling unwanted vegetation. Therefore, the invention also relates to the use of a compound of formula I or an N-oxide or an agriculturally suitable salt thereof or of a composition comprising at least one compound of for- mula I or an N-oxide or an agriculturally suitable salt thereof for combating or controlling un- wanted vegetation.
  • 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 of formula I or an N-oxide or a salt thereof to act on unwanted plants, their seed and/or their habitat.
  • the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures.
  • Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • Cis/trans isomers may be present with respect to a carbon-carbon double bond, carbon-nitrogen double bond, nitrogen-sulfur double bond (of course only if these double bonds are not part of an aromatic system) or amide group or in non-aromatic cyclic groups.
  • the term "stereoiso- mer(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 compounds of for- mula I and the stereoisomers and salts of said tautomers.
  • 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 of formula I.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention in- cludes both amorphous and crystalline compounds of formula I, their enantiomers or diastere- omers, mixtures of different crystalline states of the respective compound of formula I, its enan- tiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • Useful agriculturally suitable salts are especially the salts of those cations or the acid addi- tion 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 (NH 4 + ) and substituted am- monium in which one to four of the hydrogen atoms are replaced by Ci-C 4 -alkyl, Ci-C 4 - hydroxyalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, hydroxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isoprop- ylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetrame- thylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C 4 - alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensul- fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, car- bonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the N-oxides of compounds I are compounds in which a nitrogen atom, e.g. a ring nitro- gen atom in the group Q or a nitrogen atom of an amino group, is present in oxidized form, i.e. as a group N + -0.
  • the N-oxides are generally prepared by oxidation of the compound of formula I, e.g. with hydrogen peroxide or peroxy acids like meta-chloroperoxybenzoic acid (mCPBA), peroxyacetic acid or Caro's acid (peroxymonosulfuric acid).
  • weeds undesired vegetation
  • weeds are understood to include any vegetation grow- ing 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 - C m 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.
  • halogen atom 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • a partially or completely halogenated radical is termed below also "halo-radical”.
  • partially or completely halogenated alkyl is also termed haloalkyl.
  • alkyl refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 (“C1-C2- alkyl"), 1 to 3 (“Ci-C 3 -alkyl"),1 to 4 (“Ci-C 4 -alkyl”), 1 to 6 (“Ci-C 6 -alkyl”), 1 to 8 (“Ci-C 8 -alkyl”) or 1 to 10 (“Ci-Cio-alkyl”) carbon atoms.
  • Ci-C2-Alkyl is methyl or ethyl.
  • Ci-C3-Alkyl is additionally propyl and isopropyl.
  • Ci-C4-Alkyl is additionally n-butyl, 1-methylpropyl (sec-butyl), 2- methylpropyl (isobutyl) or 1 ,1-dimethylethyl (tert-butyl).
  • Ci-C 6 -alkyl are, in addition to those mentioned for Ci-C4-alkyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, n-hexyl, 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,
  • C-i-Cs-alkyl are, in addition to those mentioned for Ci-C 6 -alkyl, n-heptyl, 1- methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1 -ethylpentyl , 2- ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl,
  • Ci-Cio-alkyl 1.2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, and other positional isomers thereof.
  • Exam- pies for Ci-Cio-alkyl are, in addition to those mentioned for C-i-Cs-alkyl, nonyl, decyl, 2- propylheptyl, 3-propylheptyl and other positional isomers thereof.
  • haloalkyl as used herein (and in the haloalkyl moieties of other groups corn- prising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylsulfonyl and the like), which is also expressed as "alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 ("Ci-C2-haloalkyl"), 1 to 3 (“Ci-C3-haloalkyl”), 1 to 4 ("C1-C4- haloalkyl”), 1 to 6 (“Ci-C 6 -haloalkyl”), 1 to 8 (“Ci-C 8 -haloalkyl”) or 1 to 10 (“Ci-Cio-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in
  • Ci-C3-haloalkyl are, in addition to those mention for Ci-C2-haloalkyl, 1- fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 , 1 -difluoropropyl, 2,2-difluoropropyl, 1 ,2- difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trifluoroprop-2-yl, 3-chloropropyl and the like.
  • Ci-C4-haloalkyl are, in addition to those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like.
  • “Fluorinated alkyl” refers to straight-chain or branched alkyl groups having 1 to 2 (“fluori- nated Ci-C2-alkyl”), 1 to 3 (“fluorinated Ci-C3-alkyl”), 1 to 4 (“fluorinated Ci-C4-alkyl”), 1 to 6 (“fluorinated Ci-C 6 -alkyl”), 1 to 8 (“fluorinated C-i-Cs-alkyl”) or 1 to 10 (“fluorinated Ci-Cio-alkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by fluorine: in particular fluorinated Ci-C2-alkyl, such as fluoromethyl, difluorome- thyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, or pen- taflu
  • fluorinated Ci-C3-alkyl examples are, in addition to those mentioned for fluori nated Ci-C2-alkyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 ,1 -difluoropropyl, 2,2- difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl,
  • fluorinated Ci-C 4 -alkyl are, in addition to those mentioned for fluorinated Ci-C3-alkyl, 4-fluorobutyl and the like.
  • cyanoalkyl refers to straight-chain or branched alkyl groups having 1 to 4 (“Ci-C 4 -cyanoalkyl”) or 1 to 6 (“Ci-C 6 -cyanoalkyl) carbon atoms (as mentioned above), where 1 or 2, preferably 1 , of the hydrogen atoms in these groups are replaced by a cyano (CN) group.
  • CN cyano
  • Examples are cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2- cyanopropyl, 3-cyanopropyl, 1-cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl and the like.
  • alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C 2 - Cs-alkenyl"), 2 to 4 (“C 2 -C 4 -alkenyl"), 2 to 6 (“C 2 -C 6 -alkenyl”) or 2 to 8 (“C 2 -C 8 -alkenyl”) carbon atoms and a double bond in any position, for example C 2 -C3-alkenyl, such as ethenyl, prop-1 - en-1 -yl, prop-1 -en-2-yl, prop-1 -en-3-yl, or 1 -methylethenyl; C 2 -C4-alkenyl, such as ethenyl, 1 - propenyl (prop-1 -en-1 -yl), 2-propenyl (prop-1 -en-3-
  • haloalkenyl as used herein (and in the haloalkenyl moieties in haloalkenyloxy and the like), which is also expressed as "alkenyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 ("C 2 -C 3 - haloalkenyl"), 2 to 4 ("C 2 -C 4 -haloalkenyl”), 2 to 6 (“C 2 -C 6 -haloalkenyl”) or 2 to 8 (“C 2 -C 6 - haloalkenyl”) carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as men- tioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
  • alkynyl refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C 2 -C3-alkynyl”), 2 to 4 (“C 2 -C 4 -alkynyl"), 2 to 6 (“C 2 -C 6 -alkynyl”) or 2 to 8 (“C 2 -C 8 -alkynyl”) carbon atoms and a triple bond in any position, for example C 2 -C3-alkynyl, such as ethynyl, 1 -propynyl or 2-propynyl; C 2 - C 4 -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like
  • haloalkynyl as used herein (and in the haloalkynyl moieties in haloalkynyloxy and the like), which is also expressed as “alkynyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 ("C 2 -C 3 - haloalkynyl"), 2 to 4 ("C 2 -C 4 -haloalkynyl"), 3 to 4 ("C 3 -C 4 -haloalkynyl”), 2 to 6 ("C 2 -C 6 - haloalkynyl"), 3 to 6 (“C 3 -C 6 -haloalkynyl”), 2 to 8 (“C 2 -C 8 -haloalkynyl”) or 3 to 8 (“C 3 -C 8 - haloalkynyl”) carbon atoms and a triple bond in any position (as mentioned above), where some or all of
  • cycloalkyl refers to mono- or bi- or polycyclic saturated hydro- carbon radicals having 3 to 10 (“C 3 -Cio-cycloalkyl”), in particular 3 to 7 (“C 3 -C7-cycloalkyl”) or 3 to 6 (“C 3 -C 6 -cycloalkyl”) carbon atoms.
  • monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • Examples of monocyclic radicals having 3 to 10 carbon atoms comprise cyclo- propyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl.
  • Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo- [3.1.1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • halocycloalkyl as used herein, which is also expressed as “cycloalkyl which is partially or fully halogenated”, refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 7 (“C 3 -C7-halocycloalkyl”) or preferably 3 to 6 (“C 3 -C 6 -halocycloalkyl”) carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine. Examples are 1- and 2-fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl,
  • cycloalkyl-alkyl used herein denotes a cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkyl group (or inversely expressed, it denotes an alkyl group, as described above, in which one hydrogen atom is replaced by a cy- cloalkyl group, as defined above).
  • C 3 -C7-cycloalkyl-Ci-C 4 -alkyl refers to a C 3 -C 7 - cycloalkyl group as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C 4 -alkyl group, as defined above.
  • Examples are cyclo- propylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobu- tylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclo- hexylethyl, cyclohexylpropyl, cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl and the like.
  • C3-C6-cycloalkyl-Ci-C6-alkyl refers to a C3-C6-cycloalkyl group as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C 6 -alkyl group, as defined above.
  • Examples are cyclopropylmethyl, cyclopropylethyl, cyclo- propylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopen- tylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl and the like.
  • cycloalkenyl used herein denotes a monocyclic partially unsaturated, non- aromatic hydrocarbon radical.
  • Examples for C3-C6-cycloalkenyl are cycloprop-1 -en-1-yl, cyclo- prop-1 -en-3-yl, cyclobut-1-en-1-yl, cyclobut-1-en-3-yl, cyclooct-1-en-1-yl, cyclopent-1-en-1-yl, cyclopent-1-en-3-yl, cyclopent-1-en-4-yl, cyclopenta-1 ,3-dien-1-yl, cyclopenta-1 ,3-dien-2-yl, cy- clopenta-1 ,3-dien-5-yl, cyclohex-1 -en-1-yl, cyclohex-1 -en-3-yl, cyclohex-1 -en-4-yl, cyclohexa- 1
  • alkoxy denotes an alkyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C3-Alkoxy is additional ly, for example, n-propoxy and 1-methylethoxy (isopropoxy).
  • Ci-C 4 -Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1- dimethylethoxy (tert-butoxy).
  • Ci-C 6 -Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,
  • Ci-Ce-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethyl hexyl oxy and positional isomers thereof.
  • haloalkoxy denotes a haloalkyl group, as defined above, attached via an oxy- gen atom to remainder of the molecule.
  • Ci-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHC , OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoro- methoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,
  • Ci-C3-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,
  • Ci-C4-Haloalkoxy is additionally, for example,
  • Ci-C 6 -Haloalkoxy is addi- tionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
  • alkenyloxy denotes an alkenyl group, as defined above, attached via an oxy- gen atom to the remainder of the molecule.
  • C2-C6-Alkenyloxy is a C2-C6-alkenyl group, as de- fined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C8-Alkenyloxy is a C2-C8-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • haloalkenyloxy denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C6-Haloalkenyloxy is a C2-C6-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C8- Haloalkenyloxy is a C2-Cs-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • alkynyloxy denotes an alkynyl group, as defined above, attached via an oxy- gen atom to the remainder of the molecule.
  • C2-C6- Alkynyloxy is a C2-C6-alkynyl group, as de- fined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-Cs-Alkynyloxy is a C2-C8-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • haloalkynyloxy denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C6-Haloalkynyloxy is a C2-C6-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C8- Haloalkynyloxy is a C2-Cs-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C 3 -C 8 -Haloalkynyloxy is a C 3 -C 8 -haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • alkoxy-alkyl refers to a straight-chain or branched alkyl group, as defined above, where one hydrogen atom is replaced by an alkoxy group, as defined above.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Ci-C 6 -alkoxy-Ci-C 6 -alkyl refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C 6 -alkoxy group, as defined above.
  • Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec- butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1- propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert- butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1- propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl,
  • haloalkoxy-alkyl denotes a straight-chain or branched alkyl group, wherein one of the hydrogen atoms is replaced by an alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms.
  • Ci-C4-Haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g.
  • alkoxy-alkoxy refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by another alkoxy group, as defined above.
  • C1- C4-alkoxy-Ci-C4-alkoxy refers to an alkoxy group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, n-butoxymethoxy, sec-butoxymethoxy, isobutoxymethoxy, tert-butoxymethoxy, 1 - methoxyethoxy, 1 -ethoxyethoxy, 1 -propoxyethoxy, 1 -isopropoxyethoxy, 1 -n-butoxyethoxy, 1 - sec-butoxyethoxy, 1 -isobutoxyethoxy, 1 -tert-butoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2- propoxyethoxy, 2-isopropoxyethoxy, 2-n-butoxyethoxy, 2-sec-butoxyethoxy, 2-isobutoxyethoxy, 2 -tert-butoxyethoxy, 1 -methoxypropoxy, 1 -ethoxypropoxy, 1 -propoxypropoxy, 1 - isoprop
  • haloalkoxy-alkoxy denotes an alkoxy group, wherein one of the hydrogen at- oms is replaced by an alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remain- ing hydrogen atoms (either in one or in both alkoxy moieties) are replaced by halogen atoms.
  • Ci-C4-Haloalkoxy-Ci-C4-alkoxy is a Ci-C4-alkoxy group, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g.
  • Cycloalkoxy denotes a cycloalkyl group, as defined above, bound to the remainder of the molecule via an oxygen atom.
  • Examples of C3-C7-cycloalkoxy comprise cyclopropoxy, cy- clobutoxy, cyclopentoxy, cyclohexoxy and cycloheptoxy.
  • Examples of C3-Cio-cycloalkoxy corn- prise cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cy- clononoxy and cyclodecoxy.
  • cycloalkyl-alkoxy refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by a cycloalkyl group, as defined above.
  • C3- Cio-cycloalkyl-Ci-C2-alkoxy refers to an alkoxy group having 1 or 2 carbon at- oms, as defined above, where one hydrogen atom is replaced by a C3-Cio-cycloalkyl group, as defined above.
  • Examples are cyclpropylmethoxy, cyclopropylethoxy, cyclobutyl methoxy, cyclo- butylethoxy, cyclopentyl methoxy, cyclopentylethoxy, cyclohexylmethoxy, cyclohexylethoxy, cy- cloheptylmethoxy, cycloheptylethoxy, cyclooctylmethoxy, cyclooctylethoxy, cyclononylmethoxy, cyclononylethoxy, cyclodecylmethoxy and cyclodecylethoxy.
  • cycloalkyl-alkoxy-alkyl refers to an alkyl group, as defined above, wherein one hydrogen atom is replaced by an alkoxy group, as defined above, where in turn in the alkoxy group one hydrogen atom is replaced by a cycloalkyl group, as defined above.
  • C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl refers to an alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci- C 6 -alkoxy group, as defined above, where in this alkoxy group, in turn, one hydrogen atom is replaced by a C3-C6-cycloalkyl group, as defined above.
  • alkylthio (also alkylsulfanyl, “alkyl-S” or “alkyl-S(0) k “ (wherein k is 0)) as used herein denotes an alkyl group, as defined above, attached via a sulfur atom to the remainder of the molecule.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C3-Alkylthio is additionally, for exam- pie, n-propylthio or 1-methylethylthio (isopropylthio).
  • Ci-C4-Alkylthio is additionally, for example, butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1- dimethylethylthio (tert-butylthio).
  • Ci-C 6 -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,
  • C-i-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • Ci-Cio-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.
  • haloalkylthio (also haloalkylsulfanyl, “haloalkyl-S” or “haloaikyl-S(0) k “ (wherein k is 0)) as used herein denotes a haloalkyl group, as defined above, attached via a sulfur atom to the remainder of the molecule. .
  • Ci-C2-Haloalkylthio is, for example, SCFhF, SCHF2, SCF3, SCH2CI, SCHCI2, SCCI3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethyl- thio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2- fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5.
  • Ci-C3-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,
  • C1-C4- Haloalkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio.
  • Ci-C 6 -Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5- chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.
  • alkylsulfonyl denotes an alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group to the remainder of the molecule.
  • Ci-C2-Alkylsulfonyl is methylsulfonyl or ethyl- sulfonyl.
  • Ci-C3-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or 1- methylethylsulfonyl (isopropylsulfonyl).
  • Ci-C4-Alkylsulfonyl is additionally, for example, butyl- sulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl).
  • Ci-C 6 -Alkylsulfonyl is additionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 - dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 - ethylpropylsulfonyl, hexylsulfonyl, 1 -methylpentylsulfonyl, 2-methylpentylsulfonyl,
  • C-i-Cs-Alkylsulfonyl is additionally, for example, heptylsulfonyl, oc- tylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.
  • Ci-Cio-Alkylsulfonyl is additional ly, for example, nonylsulfonyl, decylsulfonyl and positional isomers thereof.
  • haloalkylsulfonyl denotes a haloalkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group to the remainder of the molecule.
  • Ci-C2-Haloalkylsulfonyl is, for example, S(0) 2 CH 2 F, S(0) 2 CHF 2 , S(0) 2 CF 3 , S(0) 2 CH 2 CI, S(0) 2 CHCI 2 , S(0) 2 CCI 3 , chlorofluoromethyl- sulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2- chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2- trifluoro
  • Ci-C 3 -Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2- difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3- trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(0) 2 CH 2 -C 2 F 5 , S(0) 2 CF 2 -C 2 F 5 , 1 -(CH 2 F)-2- fluoroethylsulfonyl, 1 -(CH 2 CI
  • C1-C4- Haloalkylsulfonyl is additionally, for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4- bromobutylsulfonyl or nonafluorobutylsulfonyl.
  • Ci-C 6 -Haloalkylsulfonyl is additionally, for exam- pie, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.
  • alkylthio-alkyl refers to a straight-chain or branched alkyl group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as de- fined above.
  • Ci-C4-alkylthio-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkylthio group, as defined above.
  • Examples are methylthiomethyl, ethyl- thiomethyl, propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, sec-butylthiomethyl, isobu- tylthiomethyl, tert-butylthiomethyl, 1 -methylthioethyl, 1 -ethylthioethyl, 1 -propylthioethyl, 1 - isopropylthioethyl, 1 -n-butylthioethyl, 1 -sec-butylthioethyl, 1 -isobutylthioethyl, 1 -tert- butylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-n- butylthioethyl, 2-sec-buty
  • alkylthio-alkylthio refers to an alkylthio group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as defined above.
  • Ci-C4-alkylthio-Ci-C4-alkylthio refers to an alkylthio group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkylthio group, as defined above.
  • Examples are methylthiomethylthio, ethylthiomethylthio, propylthiomethylthio, isopropylthiomethylthio, n-butylthiomethylthio, sec-butylthiomethylthio, isobutylthiomethylthio, tert-butylthiomethylthio, 1-methylthioethylthio, 1-ethylthioethylthio, 1-propylthioethylthio, 1- isopropylthioethylthio, 1-n-butylthioethylthio, 1-sec-butylthioethylthio, 1-isobutylthioethylthio, 1- tert-butylthioethylthio, 2-methylthioethylthio, 2-ethylthioethylthio, 2-propylthioethylthio, 2- isopropylthioethylthi
  • Ci-C3-alkylcarbonyl examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl and isopropylcarbonyl.
  • Examples for C1-C4- alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropyl- carbonyl n-butylcarbonyl and the like.
  • C-i-C3-alkylamino denotes a group -N(H)Ci-C3-alkyl.
  • C1-C4- alkylamino denotes a group -N(H)Ci-C4-alkyl.
  • Ci-C3-alkylamino are methylamino, ethylamino, propylamino and isopropylamino and the like.
  • Ci-C4-alkylamino are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.
  • di-(Ci-C3-alkyl)-amino denotes a group -N(Ci-C3-alkyl)2.
  • di-(Ci-C4- alkyl)amino denotes a group -N(Ci-C 4 -alkyl) 2 .
  • Examples are dimethylamino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylpropylamino, methylisopropylamino, ethylpropylamino, ethylisopropylamino and the like.
  • di-(Ci-C4-alkyl)amino examples are, in addition to those listed for di-(Ci-C3-alkyl)amino, n-butyl-methylamino, n-butyl-ethylamino, n- butyl-propylamino, di-n-butylamino, 2-butyl-methylamino, 2-butyl-ethylamino, 2-butyl- propylamino, isobutyl-methylamino, ethyl-isobutylamino, isobutyl-propylamino, tert-butyl- methylamino, tert-butyl-ethylamino, tert-butyl-propylamino and the like.
  • alkylamino-alkyl denotes an alkyl group, as defined above, wherein one hydro- gen atom is replaced by an alkylamino group, as defined above.
  • Ci-C4-alkylamino-Ci-C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one hydrogen atom is replaced by a C1-C4- alkylamino group, as defined above. Examples are methylaminomethyl, 1 -(methylamino)-ethyl,
  • dialkylamino-alkyl denotes an alkyl group, as defined above, wherein one hy- drogen atom is replaced by a dialkylamino group, as defined above.
  • Di-(Ci-C4-alkyl)-amino-Ci- C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one hydrogen atom is replaced by a di-(Ci-C4-alkyl)-amino group, as defined above.
  • Examples are dimethylaminomethyl, 1 - (dimethylamino)-ethyl, 2-(dimethylamino)-ethyl, 1 -(dimethylamino)-propyl, 2-(dimethylamino)- propyl, 3-(dimethylamino)-propyl, 1 -(dimethylamino)-butyl, 2-(dimethylamino)-butyl, 3- (dimethylamino)-butyl, 4-(dimethylamino)-butyl, (ethylmethylamino)-methyl, 1 - (ethylmethylamino)-ethyl, 2-(ethylmethylamino)-ethyl, 1 -(ethylmethylamino)-propyl, 2- (ethylmethylamino)-propyl, 3-(ethylmethylamino)-propyl, 1 -(ethylmethylamino
  • Ci-C3-Alkylene or Ci-C3-alkanediyl is a linear or branched divalent alkyl radical having 1 , 2 or 3 carbon atoms. Examples are -CH2-, -CH2CH2-, -CH(CH3)-, -CH2CH2CH2-, -CH(CH3)CH2-, -CH2CH(CH3)- and -C(CH3)2-.
  • Ci-C4-Alkylene or Ci-C4-alkanediyl is a linear or branched diva- lent alkyl radical having 1 , 2, 3 or 4 carbon atoms.
  • Linear Ci-C4-alkylene or Ci-C4-alkanediyl is -CH2-, -CH2CH2-, -CH2CH2CH2- or -CH2CH2CH2CH2-.
  • Heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms as ring members, i.e. atoms different from carbon.
  • these heteroatoms are N, O and S, where N and S can also be present as oxidized heteroatom groups, namely as NO, SO or SO2.
  • rings termed as heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms and/or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2 as ring members.
  • heterocyclic rings or heterocyclyl may be saturated, partially unsaturated or maximally unsaturated.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maxi- mally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heteromonocyclic rings are generally aromatic. Exceptions are maximally unsaturated 6-membered rings containing O, S, SO and/or SO2 as ring members, such as pyran and thiopyran, which are not aromatic. Par- tially unsaturated rings contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size.
  • heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • the ring contains at least one carbon ring atom. If the ring con- tains more than one O ring atom, these are not adjacent.
  • Examples of a 3-, 4-, 5-, 6- or 7-membered monocyclic saturated heterocyclic ring con- taining 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N, S, NO, S(O) and S(0) 2 as ring members include: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, 1-oxothietanyl,
  • Examples of a 3-, 4-, 5-, 6- or 7-membered monocyclic partially unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S as ring members include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4- dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4- dihydrothien-3-yl, 2-py rro I i n-2-yl , 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4
  • Examples for a 3-, 4-, 5-, 6- or 7-membered monocyclic maximally unsaturated (including aromatic) heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from the group consist- ing of O, N, S and NO as ring members are 5- or 6-membered heteroaromatic rings, such as 2- furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl,
  • Examples for a 7-, 8-, 9- or 10-membered saturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • Examples for a 7-, 8-, 9- or 10-membered partially unsaturated heterobicyclic ring contain- ing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • Examples for a 7-, 8-, 9- or 10-membered maximally unsaturated heterobicyclic ring con- taining 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • # denotes the attachment point to the remainder of the molecule.
  • the attachment point is not restricted to the ring on which is shown, but can be on either of the fused rings, and may be on a carbon or on a nitrogen ring atom. If the rings carry one or more substituents, these may be bound to carbon and/or to nitrogen ring atoms (if the latter are not part of a double bond).
  • Q is Q 1 . In another preferred embodiment, Q is Q 2 . In an- other preferred embodiment, Q is Q 3 . In another preferred embodiment, Q is Q 4 . In particular, Q is Q 1 .
  • R 1 is selected from the group consisting of halogen, nitro, cy- ano, Ci-C 4 -alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z 1 - and R 1 b -S(0) k -Z 1 -.
  • R 1 is halogen; specifically Cl.
  • R 2a is Ci-C4-haloalkyl, more preferably Ci-C3-haloalkyl and in particular C2-C3-haloalkyl.
  • C2-C3-haloalkyl the C atom bound to N does not carry any halogen atoms.
  • C2-C3-haloalkyl groups in which the C atom bound to N does not carry any halogen atoms are 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 2-fluoropropyl, 2,2-difluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3- trifluoropropyl, 2,3-difluoroethyl, 2,2,3-trifluoroethyl, 2,3,3-trifluoroethyl, 2,2,3,3-tetrafluoroethyl, 2,2,3,3,3-pentafluoroethyl, 2-fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 - methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)-e
  • haloalkyl is fluorinated alkyl.
  • R 2a is fluorinated Ci-C 4 -alkyl, even more preferably fluorinated Ci-C3-alkyl and particularly fluorinated C2-C3-alkyl.
  • fluorinated C2-C3-alkyl the C atom bound to N does not carry any fluorine atoms.
  • fluorinated C2-C3-alkyl groups in which the C atom bound to N does not carry any fluorine atoms are 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- fluoropropyl, 2,2-difluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 2,3- difluoroethyl, 2,2,3-trifluoroethyl, 2,3,3-trifluoroethyl, 2,2,3,3-tetrafluoroethyl, 2,2,3,3,3- pentafluoroethyl, 2-fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)-e
  • R 2b is selected from the group consisting of hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, where the C3-C6-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogen- ated; Ci-C4-alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. More preferably, R 2b is hydrogen or Ci-C4-alkyl. In particular, R 2b is hydrogen or Ci-C3-alkyl, more particularly hydrogen or C1-C2-
  • R 2a is Ci-C4-haloalkyl
  • R 2b is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, where the C3-C6-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C4- alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 2a is Ci-C4-haloalkyl and R 2b is hydrogen or C1-C4- alkyl.
  • R 2a is Ci-C3-haloalkyl and R 2b is hydrogen or Ci-C4-alkyl. More particularly,
  • R 2a is C2-C3-haloalkyl and R 2b is hydrogen or Ci-C3-alkyl, and even more particularly, R 2a is C2- C3-haloalkyl and R 2b is hydrogen or Ci-C2-alkyl.
  • C2-C3-haloalkyl the C atom bound to N does not carry any halogen atoms.
  • haloalkyl is preferably fluorinated alkyl. Thus, more preferably,
  • R 2a is fluorinated Ci-C 4 -alkyl
  • R 2b is selected from the group consisting of hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 2 -alkyl, where the C 3 -C 6 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C 4 - alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C 4 - alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy.
  • R 2a is fluorinated Ci-C 4 -alkyl and R 2b is hydrogen or Ci-C 4 -alkyl.
  • R 2a is fluorinated Ci-C 3 -alkyl and R 2b is hydrogen or Ci-C 4 -alkyl.
  • R 2a is fluorinated Ci-C 3 -alkyl and R 2b is hydrogen or Ci-C 3 -alkyl. Even more particularly, R 2a is fluorinated C 2 -C 3 -alkyl and R 2b is hydrogen or Ci-C 3 -alkyl. Specifically, R 2a is fluorinated C 2 -C 3 -alkyl and R 2b is hydrogen or Ci-C 2 -alkyl. In a specific embodiment, in fluorinated C 2 -C 3 -alkyl the C atom bound to N does not carry any fluorine atoms. Very specifical- ly, R 2a is CH 2 CF 3 and R 2b is hydrogen or methyl.
  • Z 2 is a covalent bond, CH 2 or CH 2 CH 2 ; and is more pref- erably CH2.
  • Z 2 is a covalent bond, CH 2 or CH 2 CH 2 ;
  • R 2a is Ci-C 4 - haloalkyl, in particular fluorinated Ci-C 4 -alkyl; and
  • R 2b is selected from the group consisting of hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 2 -alkyl, where the C 3 -C 6 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C 4 -alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci
  • Z 2 is CH 2 ;
  • R 2a is Ci-C 4 -haloalkyl, in particular fluor- inated Ci-C 4 -alkyl; and
  • R 2b is hydrogen or Ci-C 4 -alkyl.
  • Z 2 is CH 2 ;
  • R 2a is Ci-C 3 -haloalkyl, in particu- lar fluorinated Ci-C 3 -alkyl; and
  • R 2b is hydrogen or Ci-C 4 -alkyl.
  • Z 2 is CH 2 ;
  • R 2a is Ci-C 3 -haloalkyl, in particular fluorinated Ci-C 3 -alkyl, and
  • R 2b is hydrogen or Ci-C 3 -alkyl.
  • R 2a is C 2 -C 3 -haloalkyl, in particular fluorinated C 2 -C 3 -alkyl; and R 2b is hydrogen or Ci-C 3 - alkyl, in particular hydrogen or Ci-C 2 -alkyl.
  • R 2a is C 2 -C 3 -haloalkyl, in particular fluorinated C 2 -C 3 -alkyl
  • R 2b is hydrogen or Ci-C 3 - alkyl, in particular hydrogen or Ci-C 2 -alkyl.
  • the C atom bound to N does not carry any halogen/fluorine atoms.
  • Z 2 is CFh; R 2a is C 2 -C 3 -haloalkyl where the C atom bound to N does not carry any halogen atoms; and R 2b is hydrogen or Ci-C 3 -alkyl.
  • Z 2 is CFh; R 2a is fluorinated C 2 -C 3 -alkyl where the C atom bound to N does not carry any fluorine atoms; and R 2b is hydrogen or Ci-C 3 -alkyl.
  • Z 2 is CH 2 ;
  • R 2a is fluorinated C 2 -C 3 -alkyl where the C atom bound to N does not carry any fluorine at- oms; and
  • R 2b is hydrogen or Ci-C 2 -alkyl.
  • Z 2 is CH 2 ;
  • R 2a is CH 2 CF 3 and R 2b is hydrogen or methyl.
  • R 3 is selected from the group consisting of halogen, nitro, C 1 - C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -haloalkoxy-Z 3 and R 3b -S(0) k -Z 3 ; in particular from halogen and Ci-C 4 -alkylsulfonyl; specifically from Cl and methylsulfonyl; and is very specifically Cl.
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C 2 -alkyl, and Ci-C 2 -haloalkyl. More preferably, R 4 is selected from the group consisting of hydrogen, cyano, chlorine, fluorine and CH 3 . In particular, R 4 is hydrogen.
  • each R 5 is independently selected from the group consisting of CrCe-alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl and phenyl; more preferably from Ci-C 4 -alkyl,
  • Q is Q 1 ; R 1 is halogen; in R 2 Z 2 is a covalent bond or CFh; R 2a is Ci-C 4 -haloalkyl, in particular fluorinated Ci-C 4 -alkyl; R 2b is hydrogen or Ci-C 4 -alkyl; R 3 is Cl or Ci-C 4 -alkylsulfonyl; R 4 is hydrogen; and R 5 is Ci-C 4 -alkyl.
  • Q is Q 1 ; R 1 is Cl; in R 2 Z 2 is CH 2 ; R 2a is Ci-C 3 -haloalkyl, in particular fluorinated Ci-C 3 -alkyl; R 2b is hydrogen or C 1 - C 3 -alkyl; R 3 is Cl; R 4 is hydrogen; and R 5 is methyl.
  • Q is Q 1 ; R 1 is Cl; in R 2 Z 2 is CH 2 ; R 2a is C 2 -C 3 -haloalkyl, in particular fluorinated C 2 -C 3 -alkyl; R 2b is hydrogen or Ci-C 3 -alkyl;
  • R 3 is Cl; R 4 is hydrogen; and R 5 is methyl. More specifically, Q is Q 1 ; R 1 is Cl; in R 2 Z 2 is Chh;
  • R 2a is fluorinated C 2 -C 3 -alkyl, where the C atom bound to N does not carry any fluorine atoms;
  • R 2b is hydrogen or Ci-C 2 -alkyl;
  • R 3 is Cl;
  • R 4 is hydrogen; and
  • R 5 is methyl.
  • Q is Q 1 ;
  • R 1 is Cl; in R 2 Z 2 is Chh;
  • R 2a is CH 2 CF 3 ;
  • R 2b is hydrogen or methyl;
  • R 3 is Cl;
  • R 4 is hydrogen; and R 5 is methyl.
  • R 11 , R 21 are preferably selected from halogen, Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkylthio-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy and Ci-C 6 -haloalkyloxy, more preferably from halogen, Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, Ci-C 4 -haloalkyl and Ci-C 4 -alkoxy.
  • R 11 , R 21 independently of each other are selected from the group consisting of halogen, C 1 -C 4 - alkyl, C 3 -C 6 -cycloalkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkylthio- Ci-C 4 -alkyl and Ci-C 4 -alkoxy-Ci-C 4 -alkoxy; in particular from halogen, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl and Ci-C 4 -alkoxy-Ci-C 4 -alkoxy; and specifically from Cl, F, Br, methyl, ethyl, methoxy and trifluoromethyl.
  • R 22 is preferably selected from hydrogen, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -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 the rings of phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which
  • R 22 is selected from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 - alkynyl, C 3 -C 6 -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 22 is selected from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 - haloalkenyl, C 3 -C 6 -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 23 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C 6 -alkenyl, C 3 - C6-cycloalkyl and phenyl. More preferably R 23 is selected from hydrogen, Ci-C 4 -alkyl, C 1 -C 4 - haloalkyl and C 3 -C 6 -cycloalkyl; and in particular, R 23 is selected from hydrogen, Ci-C 3 -alkyl and Ci-C 3 -haloalkyl.
  • R 24 is preferably selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl and phenyl. More preferably R 24 is selected from Ci-C 4 -alkyl, Ci-C 4 -haloalkyl and C 3 -C 6 - cycloalkyl; and in particular R 23 is selected from Ci-C 3 -alkyl and Ci-C 3 -haloalkyl.
  • R 25 is preferably selected from Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 - haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 4 -alkoxy-Ci- C 4 -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 the rings of phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are
  • R 25 is selected from Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -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 25 is selected from Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 3 -C 6 -cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • Z 1 , Z 3 are preferably selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.
  • Z 3a is preferably selected from a covalent bond, Ci-C 2 -alkanediyl, 0-Ci-C 2 -alkanediyl, Ci- C 2 -alkanediyl-0 and Ci-C 2 -alkanediyl-0-Ci-C 2 -alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyl, O-ethanediyl, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.
  • R b , R 1b , R 3b independently of each other, are preferably selected from Ci-C 6 -alkyl, C 3 -C 7 - cycloalkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -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-C 4 -alkyl, Ci-C 2 -haloalkyl
  • R b , R 1b , R 3b are selected from the group consisting of Ci-C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, Ci-C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 - C 4 -haloalkynyl, C 3 -C 6 -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 3b independently of each other, are selected from Ci-C 4 -alkyl, C 1 - C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -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 3c , R k independently of each other, are preferably selected from hydrogen, Ci-C 6 -alkyl, C 3 -C 7 -cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -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
  • R 3c , R k are selected from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -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 3c , R k ⁇ independently of each other, are selected from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 - alkenyl, C 2 -C 4 -haloalkenyl, C 3 -C 6 -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 3d is preferably selected from Ci-C 6 -alkyl, C 3 -C 7 -cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl and benzyl.
  • R 3d is selected from Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 1 - C 4 -alkoxy-Ci-C 4 -alkyl and C 3 -C 7 -cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 - haloalkenyl, C 2 -C 4 -alkynyl and C 3 -C 6 -cycloalkyl.
  • R 3e , R 3f independently of each other, are preferably selected from the group consisting of hydrogen, Ci-C 6 -alkyl, C 3 -C 7 -cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, Ci-C 4 -alkoxy-Ci-C 4 -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-C 4 -alkyl, C 1 -C 4 - haloalkyl and Ci-C 4 -alkoxy, or R 3e and R 3f together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated
  • R 3e , R 3f independently of each other, are selected from hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl and benzyl, or R 3e and R 3f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated 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-C 4 -alkyl and Ci-C 4 -haloalkyl.
  • R 3e , R 3f independently of each other, are selected from hydrogen and Ci-C 4 -alkyl, or R 3e and R 3f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated 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.
  • R3 ⁇ 4 is preferably selected from hydrogen, Ci-C6-alkyl, C 3 -C 7 -cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl and benzyl.
  • R3 ⁇ 4 is selected from hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 - C 6 -haloalkenyl, benzyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl and C 3 -C 7 -cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C 4 -alkyl, C 1 -C 4 - haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, benzyl and C 3 -C 6 -cycloalkyl.
  • R 3h is selected from hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, benzyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl and C 3 -C 7 -cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 - alkenyl, C 2 -C 4 -haloalkenyl, benzyl and C 3 -C 6 -cycloalkyl; or R3 ⁇ 4 and R 3h together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from
  • R z is preferably selected from Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C3-C7-cycloalkyl, Ci-C 6 -alkoxy, C2-C6-alkenyl, phenyl, benzyl, heterocyclyl and heterocyclylmethyl, where heterocyclyl in the last two mentioned radicals 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 unsubstitut- ed or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R z is selected from of Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are iden- tical or different and selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy.
  • R z is Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy, phenyl or ben- zyl, where phenyl and benzyl are unsubstituted or substituted by 1 or 2 groups, which are identi- cal or different and selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl; and in particular R z is Ci-C3-alkyl, Ci-C3-haloalkyl or Ci-C4-alkoxy.
  • n is in particular 0 or 2.
  • variable k is in particular 0 or 2, and especially 2.
  • Examples of preferred compounds are the compounds of formulae l.a, l.b, l.c, l.d. I.e, l.f, l.g, l.h, l.i, l.j, l.k and 1.1, wherein for an individual compound the variables are as defined in one row of table 1 . Moreover, the meanings mentioned below for the individual variables in table 1 are per se, independently of the combination in which they are mentioned, a particularly pre- ferred embodiment of the substituents in question.
  • the invention relates to compounds I selected from the corn- pounds of the examples, either in form of free bases or of any agriculturally suitable salt thereof or a stereoisomer, the racemate or any mixture of stereoisomers thereof or a tautomer or a tau- tomeric mixture or an N-oxide thereof.
  • the compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described in the schemes below.
  • the substituents, variables and indices used in the schemes are as defined above for the compounds of formula I, if not specified oth- erwise.
  • Phenolic benzamide compounds of formula II can be reacted with compounds R 2 -X to af- ford compounds of the formula I.
  • X is a suitable leaving group, such as halogen, in particular Cl.
  • Suitable bases are for example carbonates, such as lithium, sodium or potassium car- bonates, 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 apro- tic solvents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloro- form, 1 ,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trime- thylbenzene, pyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1 ,4-dioxane, N,N-dimethyl formamide, N-methyl pyrrolidinone or mixtures thereof.
  • the starting materials are generally re- acted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range
  • Y is a leaving group, such as halogen, in particular Cl, an anhydride residue or an active ester residue.
  • X being halogen
  • the reaction is suitably carried out in the presence of a base.
  • bases are for example carbonates, such as lithi- um, 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, cyclohex- ane, dichloromethane, chloroform, 1 ,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trimethylbenzene, 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 there- of.
  • the starting materials are generally reacted with one another in equimolar or nearly equimo- lar amounts at a reaction temperature usually in the range of -20°
  • the reaction is preferably carried out in the presence of a suitable activating agent which converts the acid group of compound IV into an activated ester or amide.
  • 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 1 ,T,carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3-dimethylamino- propyl)carbodiimide (EDC) or 2,4,6-tripropyM ,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) can be employed.
  • the activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting compound IV with the activating agent in the presence of compound III, or in a separate step prior to the reaction with compound III. It may be advantageous, especially in cases where DCC or EDC are used as activating agent, to include further additives in the activating reaction, such as hydroxybenzotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4,5-trichlorophenol or N-hydroxysuccinimide. It may further be advantageous to prepare the activated ester or amide in the presence of a base, for example a tertiary amine.
  • a base for example a tertiary amine.
  • the activated ester or amide is either in situ or subsequently reacted with the amine of formula III to afford the amide of formula I.
  • the reaction normally takes place in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. dichloromethane or dichlo- roethane, ethers, e.g. tetrahydrofuran or 1 ,4-dioxane, or carboxamides, e.g. N,N-dimethylform- amide, N,N-dimethylacetamide or N-methylpyrrolidone.
  • the reaction is ordinarily carried out at temperatures in the range from -20°C to +25°C.
  • Phenolic benzamide compounds of formula II may be converted with phosgene to the cor- responding chloroformate which can subsequently be reacted with the amine of formula V to give the desired benzamide carbamate of formula G.
  • invert solvents are used for both reaction steps 1 ) and 2) invert solvents. Both reaction steps are usually carried out at temperatures of about -50°C to 30°C in the presence of a base, such as a tertary amine, e.g. trimethylamine, or pyri dine.
  • the compounds of formula G can also be prepared according procedures described in via the synthetic route depicted in Scheme 4 below, using procedures of T. Patonay et al., Synth. Commun. 1990, 20, 2865-2885.
  • 1 -Chloromethyl carbonates of the formula VII can be reacted with amines of formula V to afford the corresponding benzamide carbamate of formula G.
  • the reaction is generally run in tetrahydrofuran or dioxane in the presence of a base, such as in particular an aqueous solution of potassium carbonate, at a temperature of about -10°C to 40°C.
  • the compound of formula VII can be obtained by treating the corresponding 1 -chloroalkyl chloroformate with a phenolic ben- zamide compound of formula II in the presence of a base, such as in particular pyridine.
  • the compounds of formula I’ with R 2b being hydrogen can also be prepared as shown in
  • Phenolic benzamide compounds of formula II may be converted with isocyanates of for- mula VIII to the benzamide carbamate of the formula IX, which is a compound of formula I’, wherein R 2b is hydrogen.
  • the reaction is generally carried out in an invert solvent with a suitable base, e.g. triethylamine, being present.
  • the phenolic benzamide compounds of formula II can be prepared using a synthesis route that includes the intermediate protection of the hydroxyl group.
  • step 1 the hydroxyl group of the phenol derivative of formula X is protected by introduc- ing a suitable protective group, such as in particular a benzyl group.
  • a suitable protective group such as in particular a benzyl group.
  • This conversion is typically achieved via reaction with a benzyl halide, such as in particular benzyl bromide, in the presence of a base.
  • Suitable bases are for example carbonates, such as in particular potassium car- bonate.
  • the reaction can be carried out in an aprotic solvent, such as acetone, at a temperature in the range of about 0°C to 100°C.
  • step 2) the benzyl protected compound obtained in step 1 ) is first treated with a strong base, in particular an organolithium base, such as n-butyllithium or lithium diisopropylamide, and afterwards reacted with carbon dioxide to afford to benzoic acid derivative of formula XI.
  • a strong base in particular an organolithium base, such as n-butyllithium or lithium diisopropylamide
  • Suita- ble solvents are inert ones, such as in particular THF. The reaction is started at a temperature in the range of -100°C to -50°C and concluded at about -10°C to 30°C.
  • step 3) the benzoic acid derivative of formula XI is activated by conversion to a suitable ester or amide, or preferably to a suitable acid halide, by analogy with the synthesis described in Scheme 2.
  • step 4) the activated benzoic acid derivative of formula XII obtained in step 3) is ami- dated with an amine of formula III by analogy with the synthesis described in Scheme 2. Ac- cordingly, steps 3) and 4) may also be carried in situ or even simultaneously.
  • step 5 The removal of the protecting group is achieved in step 5), in case PG is a benzyl group, for instance by subjecting the amidation product obtained in step 4) to strong acidic conditions to afford the phenolic benzamide of formula II.
  • Scheme 8 depicts a specific synthetic route towards compounds of the formula IV wherein Z 2 in the radical R 2 is a dimethylmethylene bridge (-C(CH3)2-).
  • Z 2 in the radical R 2 is a dimethylmethylene bridge (-C(CH3)2-).
  • Such compounds are termed in the following compounds of the formula IV’ and may serve as precursor for compounds of the formula I having such a substituent R 2 .
  • the Bargellini reaction can be used to convert the phenol derivative of formula X into a compound of formula XIII by reacting it with acetone and chloroform in the presence of a base, e.g. an alkali metal hydroxide, such as sodium hydroxide, at a temperature in the range of 10°C to 80°C.
  • a base e.g. an alkali metal hydroxide, such as sodium hydroxide
  • Acetone typically also serves as solvent and can therefore be used in excess.
  • step 2 can be accomplished, for instance, by converting the compound of formula XIII in analogy with the reaction described in Scheme 2 into the corresponding acid halide, which is then treated with the amine of formula V to afford a compound of formula XIV.
  • step 3 The carboxylation in step 3) can be carried out analogously to the reaction shown in
  • 5-amino-1-R 5 -tetrazole compounds of formula lll-a can be prepared accord- ing to the method described in the Journal of the American Chemical Society, 1954, 76, 88-89 (Scheme 10).
  • 5-Amino-1 -R 5 -triazoles of formula lll-b are either commercially available or are obtainable according to methods described in the literature. As shown in Scheme 1 1 , 5-amino-1 -R 5 -triazole can for example be prepared from 5-aminotriazole according to the method described in Zeitschrift fur Chemie, 1990, 30, 12, 436-437.
  • 5-amino-1 -R 5 -triazole compounds of formula lll-b can also be prepared analogously to the synthesis described in Chemische Berichte, 1964, 97, 2, 396-404, as shown in Scheme 12.
  • 4-amino-1 ,2,5-oxadiazole compounds of the formula lll-c are either commercially available or are obtainable according to methods known from the literature.
  • 3- alkyl-4-amino-1 ,2,5-oxadiazoles can be prepared from b-ketoesters pursuant to a procedure described in Russian Chemical Bulletin, Int. Ed., 54(4), 1032-1037 (2005), as depicted in Scheme 13.
  • the compounds of the formula lll-c, where R 5 is halogen can be prepared from commercially available 3, 4-diamino-1 ,2,5-oxadiazole according to procedures described in the literature, e.g. by the Sandmeyer-type reaction disclosed in Heteroatom Chem- istry, 15(3), 199-207 (2004).
  • the compounds of the formula lll-c, where R 5 is a nucleophilic residue can be prepared by introducing the nucleophilic residue via the substitution of a leaving group L, e.g. halogene, in the 4-position of the 1 ,2,5-oxadiazoles compounds of formula XV in accordance to precedures disclosed, for example, in Journal of Chemical Research, Synopses (6), 190 (1985), in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (9), 2086-8 (1986) or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614 (2004).
  • L e.g. halogene
  • compounds of formulae 111 -a , lll-b and lll-c can be obtained by purchase or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO
  • the compounds of formula I including their stereoisomers, salts and tautomers, as well as their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds cannot 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 corn- pounds 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, re- duction, 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 chromatog- raphy, for example on alumina or on silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystal I iza- tion or trituration.
  • the compounds of formula I and their agriculturally suitable salts are useful as herbicides. They are useful as such or as an appropriately formulated composition.
  • the herbicidal composi- tions comprising the compound I, in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • the compounds of formula I, in particu- lar the preferred aspects thereof, or compositions comprising them can additionally be em- ployed 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, muta- genesis 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, mu- tations or natural recombination (i.e. reassembly of the genetic information).
  • one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.
  • crop plants also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, US 5,013,659) or imidazolinones (see, for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527,
  • herbicides such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, US 5,013,659) or imidazolinones (see, for example, US 6,222,
  • 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).
  • crop plants refers to plants that comprise in their genomes a gene encoding a herbicide-tolerant wild-type or mutated HPPD protein.
  • a gene may be an endogenous gene or a transgene, as described hereinafter.
  • a “herbicide-tolerant” or “herbicide-resistant” plant it is intended that a plant that is tol- erant or resistant to at least one herbicide at a level that would normally kill, or inhibit the growth of, a normal or wild-type plant.
  • “herbicide-tolerant wild-type or mutated HPPD protein” or “herbicide -resistant wild-type or mutated HPPD protein” it is intended that such a HPPD pro- tein displays higher HPPD activity, relative to the HPPD activity of a wild-type or reference HPPD protein, when in the presence of at least one herbicide that is known to interfere with HPPD activity and at a concentration or level of the herbicide that is known to inhibit the HPPD activity of the reference wild-type HPPD protein.
  • the HPPD activity of such a herb- icide-tolerant or herbicide-resistant HPPD protein may be referred to herein as “herbicide- tolerant” or “herbicide-resistant” HPPD activity.
  • mutated HPPD nucleic acid refers to an HPPD nucleic acid having a sequence that is mutated from a wild-type HPPD nucleic acid and that confers increased“ HPPD-inhibiting herbicide” tolerance to a plant in which it is expressed.
  • mutated hy- droxyphenyl pyruvate dioxygenase refers to the replacement of an amino acid of the wild-type primary sequences SEQ ID NO: 2, 5, 8, 11 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, a vari- ant, a derivative, a homologue, an orthologue, or paralogue thereof, with another amino acid.
  • the expression "mutated amino acid” will be used below to designate the amino acid which is replaced by another amino acid, thereby designating the site of the mutation in the primary se- quence of the protein.
  • HPPDs and their primary sequences have been described in the state of the art, in particular the HPPDs of bacteria such as Pseudomonas (Ruetschi etal., Eur.J.Biochem., 205, 459-466, 1992, W096/38567), of plants such as Arabidopsis (W096/38567, Genebank
  • the nucleotide sequence of (i) comprises the sequence of SEQ ID NO: 1 , 51 , 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21 , 23, 25, 27, 29, 31 , 33, 35, 37, 39, 41 , 43, 45, 47, 49, 52, 54, 56, 68, 69 or a variant or derivative thereof.
  • the mutated HPPD nucleic acid useful for the pre- sent invention comprises a mutated nucleic acid sequence of SEQ ID NO: 1 or SEQ ID NO: 52, or a variant or derivative thereof.
  • nucleotide sequences of (i) or (ii) encompass homologues, paralogues and orthologues of SEQ ID NO: 1 , 51 , 3, 4, 6,
  • variants with respect to a sequence (e.g., a polypeptide or nucleic acid sequence such as - for example - a transcription regulating nucleotide sequence of the invention) is intended to mean substantially similar sequences.
  • variants include those sequences that, because of the degeneracy of the genetic code, encode the identical amino acid sequence of the native protein.
  • Naturally occur- ring allelic variants such as these can be identified with the use of well-known molecular biology techniques, as, for example, with polymerase chain reaction (PCR) and hybridization tech- niques.
  • Variant nucleotide sequences also include synthetically derived nucleotide sequences, such as those generated, for example, by using site-directed mutagenesis and for open reading frames, encode the native protein, as well as those that encode a polypeptide having amino acid substitutions relative to the native protein.
  • nucleotide sequence variants of the invention will have at least 30, 40, 50, 60, to 70%, e.g., preferably 71 %, 72%, 73%, 74%, 75%, 76%, 77%, 78%, to 79%, generally at least 80%, e.g., 81 %-84%, at least 85%, e.g., 86%, 87%, 88%, 89%, 90%, 91 %, 92%, 93%, 94%, 95%, 96%, 97%, to 98% and 99% nucleotide“ se- quence identity” to the nucleotide sequence of SEQ ID NO:1 , 51 , 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21 , 23, 25, 27, 29, 31 , 33, 35, 37, 39, 41 , 43, 45, 47, 49, 52, 54, 56, 68, 69, 47, or 49.
  • variant polypeptide is intended a polypeptide derived from the protein of SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, by deletion (so-called truncation) or addition of one or more ami- no acids to the N-terminal and/or C-terminal end of the native protein; deletion or addition of one or more amino acids at one or more sites in the native protein; or substitution of one or more amino acids at one or more sites in the native protein.
  • Such variants may result from, for exam- pie, genetic polymorphism or from human manipulation. Methods for such manipulations are generally known in the art.
  • variants of the polynucleotides useful for the present invention will have at least 30, 40, 50, 60, to 70%, e.g., preferably 71 %, 72%, 73%, 74%, 75%, 76%, 77%, 78%, to 79%, generally at least 80%, e.g., 81 %-84%, at least 85%, e.g., 86%, 87%, 88%, 89%, 90%, 91 %, 92%, 93%, 94%, 95%, 96%, 97%, to 98% and 99% nucleotide“ sequence identi ty” to the nucleotide sequence of SEQ ID NO:1 , 47, 49, or SEQ ID NO: 52.
  • polynucleotide molecules and polypeptides of the invention encompass polynucleotide molecules and polypeptides comprising a nucleotide or an amino acid sequence that is sufficiently identical to nucleotide sequences set forth in SEQ ID NOs: 1 , 51 , 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21 , 23, 25, 27, 29, 31 , 33, 35, 37, 39, 41 , 43, 45, 47, 49, 52, 54, 56, 68, 69, 47, or 49, or to the amino acid sequences set forth in SEQ ID NOs: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63,
  • the term "sufficiently identical" is used herein to refer to a first amino acid or nucleotide sequence that contains a sufficient or minimum number of identical or equiva- lent (e.g., with a similar side chain) amino acid residues or nucleotides to a second amino acid or nucleotide sequence such that the first and second amino acid or nucleotide sequences have a common structural domain and/or common functional activity.
  • Sequence identity refers to the extent to which two optimally aligned DNA or amino acid se- quences are invariant throughout a window of alignment of components, e.g., nucleotides or amino acids.
  • An "identity fraction” for aligned segments of a test sequence and a reference se- quence is the number of identical components that are shared by the two aligned sequences divided by the total number of components in reference sequence segment, i.e., the entire ref- erence sequence or a smaller defined part of the reference sequence. "Percent identity” is the identity fraction times 100.
  • Optimal alignment of sequences for aligning a comparison window are well known to those skilled in the art and may be conducted by tools such as the local ho- mology algorithm of Smith and Waterman, the homology alignment algorithm of Needleman and Wunsch, the search for similarity method of Pearson and Lipman, and preferably by computer- ized implementations of these algorithms such as GAP, BESTFIT, FASTA, and TFASTA availa- ble as part of the GCG. Wisconsin Package. (Accelrys Inc. Burlington, Mass.)
  • nucleic acid sequence(s) refers to nucleotides, either ribonucleotides or deoxyribonucleotides or a combination of both, in a polymeric un- branched form of any length.
  • Derivatives of a protein encompass peptides, oligopeptides, polypeptides, proteins and en- zymes having amino acid substitutions, deletions and/or insertions relative to the unmodified protein in question and having similar biological and functional activity as the unmodified protein from which they are derived.
  • Homologues of a protein encompass peptides, oligopeptides, polypeptides, proteins and en- zymes having amino acid substitutions, deletions and/or insertions relative to the unmodified protein in question and having similar biological and functional activity as the unmodified protein from which they are derived.
  • a deletion refers to removal of one or more amino acids from a protein.
  • Insertions refers to one or more amino acid residues being introduced into a predetermined site in a protein. Insertions may comprise N-terminal and/or C-terminal fusions as well as intra- sequence insertions of single or multiple amino acids. Generally, insertions within the amino acid sequence will be smaller than N- or C-terminal fusions, of the order of about 1 to 10 resi- dues.
  • N- or C-terminal fusion proteins or peptides include the binding domain or activation domain of a transcriptional activator as used in the yeast two-hybrid system, phage coat proteins, (histidine)-6-tag, glutathione S-transferase-tag, protein A, maltose-binding protein, dihydrofolate reductase, Tag ⁇ 100 epitope, c-myc epitope, FLAG ® -epitope, lacZ, CMP (cal- modulin-binding peptide), HA epitope, protein C epitope and VSV epitope.
  • a transcriptional activator as used in the yeast two-hybrid system
  • phage coat proteins phage coat proteins
  • glutathione S-transferase-tag glutathione S-transferase-tag
  • protein A maltose-binding protein
  • dihydrofolate reductase Tag ⁇ 100 epitope
  • a substitution refers to replacement of amino acids of the protein with other amino acids having similar properties (such as similar hydrophobicity, hydrophilicity, antigenicity, propensity to form or break a -helical structures or b -sheet structures).
  • Amino acid substitutions are typically of single residues, but may be clustered depending upon functional constraints placed upon the polypeptide and may range from 1 to 10 amino acids; insertions will usually be of the order of about 1 to 10 amino acid residues.
  • the amino acid substitutions are preferably conservative amino acid substitutions. Conservative substitution tables are well known in the art (see for ex- ample Creighton (1984) Proteins. W.H. Freeman and Company (Eds).
  • Amino acid substitutions, deletions and/or insertions may readily be made using peptide syn- thetic techniques well known in the art, such as solid phase peptide synthesis and the like, or by recombinant DNA manipulation. Methods for the manipulation of DNA sequences to produce substitution, insertion or deletion variants of a protein are well known in the art. For example, techniques for making substitution mutations at predetermined sites in DNA are well known to those skilled in the art and include M13 mutagenesis, T7-Gen in vitro mutagenesis (USB, Cleve- land, OH), QuikChange Site Directed mutagenesis (Stratagene, San Diego, CA), PCR-mediated site-directed mutagenesis or other site-directed mutagenesis protocols.
  • “Derivatives” further include peptides, oligopeptides, polypeptides which may, compared to the amino acid sequence of the naturally-occurring form of the protein, such as the protein of inter- est, comprise substitutions of amino acids with non-naturally occurring amino acid residues, or additions of non-naturally occurring amino acid residues.
  • “Derivatives” of a protein also encom- pass peptides, oligopeptides, polypeptides which comprise naturally occurring altered (glycosyl- ated, acylated, prenylated, phosphorylated, myristoylated, sulphated etc.) or non-naturally al- tered amino acid residues compared to the amino acid sequence of a naturally-occurring form of the polypeptide.
  • a derivative may also comprise one or more non-amino acid substituents or additions compared to the amino acid sequence from which it is derived, for example a reporter molecule or other ligand, covalently or non-covalently bound to the amino acid sequence, such as a reporter molecule which is bound to facilitate its detection, and non-naturally occurring amino acid residues relative to the amino acid sequence of a naturally-occurring protein.
  • a reporter molecule or other ligand covalently or non-covalently bound to the amino acid sequence, such as a reporter molecule which is bound to facilitate its detection, and non-naturally occurring amino acid residues relative to the amino acid sequence of a naturally-occurring protein.
  • “derivatives” also include fusions of the naturally-occurring form of the protein with tagging peptides such as FLAG, HIS6 or thioredoxin (for a review of tagging peptides, see Ter- pe, Appl. Microbiol. Biotechnol. 60,
  • orthologues and “paralogues” encompass evolutionary concepts used to describe the ances- tral relationships of genes. Paralogues are genes within the same species that have originated through duplication of an ancestral gene; orthologues are genes from different organisms that have originated through speciation, and are also derived from a common ancestral gene.
  • paralogues and orthologues may share distinct domains harboring suitable amino acid residues at given sites, such as binding pockets for particular substrates or binding motifs for interaction with other proteins.
  • domain refers to a set of amino acids conserved at specific positions along an alignment of sequences of evolutionarily related proteins. While amino acids at other positions can vary between homologues, amino acids that are highly conserved at specific positions indi cate amino acids that are likely essential in the structure, stability or function of a protein. Iden- tified by their high degree of conservation in aligned sequences of a family of protein homo- logues, they can be used as identifiers to determine if any polypeptide in question belongs to a previously identified polypeptide family.
  • motif or "consensus sequence” refers to a short conserved region in the sequence of evolutionarily related proteins. Motifs are frequently highly conserved parts of domains, but may also include only part of the domain, or be located outside of conserved domain (if all of the amino acids of the motif fall outside of a defined domain).
  • Homologues may readily be identified using, for example, the ClustalW multiple sequence alignment algorithm (version 1.83), with the default pairwise alignment parameters, and a scoring method in percentage. Global percent- ages of similarity and identity may also be determined using one of the methods available in the MatGAT software package (Campanella et al., BMC Bioinformatics. 2003 Jul 10;4:29. MatGAT: an application that generates similarity/identity matrices using protein or DNA sequences.).
  • the herbicide tolerance or re- sistance of a plant to the herbicide as described herein could be remarkably increased as corn- pared to the activity of the wild type HPPD enzymes with SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67.
  • Preferred substitutions of mutated HPPD are those that increase the herbicide tolerance of the plant, but leave the biological activitiy of the dioxygenase activity substantially unaffected.
  • the mutated HPPD useful for the present invention comprises a sequence of SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, or a variant, derivative, orthologue, paralogue or homo- logue thereof, wherein an amino acid ⁇ 3, ⁇ 2 or ⁇ 1 amino acid positions from a key amino acid is substituted by any other amino acid.
  • a highly characteristic sequence pattern can be de- veloped, by means of which further of mutated HPPD candidates with the desired activity may be searched.
  • the present sequence pattern is not limited by the exact distances between two adjacent amino acid residues of said pattern.
  • Each of the distances between two neighbours in the above patterns may, for example, vary independently of each other by up to ⁇ 10, ⁇ 5, ⁇ 3, ⁇ 2 or ⁇ 1 amino acid positions without substantially affecting the desired activity.
  • the mutated HPPD refers to a variant or derivative of SEQ ID NO: 2 wherein the substitutions are selected from the following Table 4a.
  • Table 4a (Sequence ID No: 2): single amino acid substitutions
  • the herbicide tolerance or resistance could be remarkably increased as compared to the activity of the wild type HPPD enzymes or HPPD enzymes in which only one amino acid residue had been substituted. Therefore, in another preferred embodiment, the vari- ant or derivative of the mutated HPPD refers to a polypeptide of SEQ ID NO: 2, wherein two, three, four or five key amino acids are substituted by another amino acid residue. Particularly preferred double, triple, quadruple, or quintuple mutations are described in Table 4b. Table 4b: (with reference to Sequence ID No: 2): combined amino acid substitutions
  • the mutated HPPD refers to a polypeptide comprising SEQ ID NO: 2, wherein the leucine corresponding to or at position 320 is substituted by a histidine, and the proline corresponding to or at position 321 is substituted by an alanine.
  • the mutated HPPD refers to a polypep- tide comprising SEQ ID NO: 2, wherein Leucine corresponding to or at position 353 is substitut- ed by a Methionine, the Proline corresponding to or at position 321 is substituted by an Argi- nine, and the Leucine corresponding to or at position 320 is substituted by an Asparagine.
  • the mutated HPPD refers to a polypep- tide comprising SEQ ID NO: 2, wherein the Leucine corresponding to or at position 353 is sub- stituted by a Methionine, the Proline corresponding to or at position 321 is substituted by an Arginine, and the Leucine corresponding to or at position 320 is substituted by a glutamine.
  • the mutated HPPD refers to a variant or derivative of SEQ ID NO: 53 wherein the substitutions are selected from the following Table 4c.
  • the variant or derivative of the mutated HPPD useful for the present invention refers to a polypeptide of SEQ ID NO: 53, a homologue, orthologue, or pa- ralogue thereof, wherein two, three, four or five key amino acids are substituted by another ami- no acid residue.
  • Particularly preferred double, triple, quadruple, or quintuple mutations are de- scribed in Table 4d.
  • the mutated HPPD of the present invention comprises a vari- ant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, which comprises one or more of the following:
  • the amino acid corresponding to or at position 30 is other than proline
  • the amino acid corre- sponding to or at position 39 is other than Phe
  • the amino acid corresponding to or at position 54 is other than Gly
  • the amino acid corresponding to or at position 57 is other than Met
  • the amino acid corresponding to or at position 84 is other than Phe
  • the amino acid corresponding to or at position 210 is other than Val
  • the amino acid corresponding to or at position 212 is oth- er than Asn
  • the amino acid corresponding to or at position 223 is other than Val
  • the amino acid corresponding to or at position 243 is other than Val
  • the amino acid corresponding to or at posi- tion 247 is other than Leu
  • the amino acid corresponding to or at position 249 is other than Ser
  • the amino acid corresponding to or at position 251 is other than Val
  • the amino acid correspond- ing to or at position 264 is other than Asn
  • the amino acid corresponding to or at position 291 is other
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 367 is Val
  • amino acid corresponding to or at position 375 is Leu.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 367 is Val
  • amino acid corresponding to or at position 375 is Leu
  • amino acid corresponding to or at position 39 is Leu.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 367 is Val
  • amino acid corresponding to or at position 375 is Leu
  • amino acid corresponding to or at position 39 is Trp.
  • the mutated HPPD comprises a variant of the sequence of
  • SEQ ID NO: 50 or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 345 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie,
  • the mutated HPPD comprises a variant of the sequence of
  • SEQ ID NO: 50 or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 345 is Gin, and the amino acid corresponding to or at position 341 is lie.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 345 is Gin, and the amino acid corresponding to or at position 326 is Glu.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 345 is Gin
  • the amino acid corresponding to or at position 326 is Asp.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 345 is Gin
  • the amino acid corresponding to or at position 326 is Gin.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 318 is Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Pro.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 319 is Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, Val, particularly preferred Pro.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 318 is Pro
  • amino acid corresponding to or at position 319 is Pro
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 321 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 350 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Met.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 405 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 251 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr, particularly preferred Ala.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 317 is Ala, Arg, Asn, Asp, Cys, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred His or Met.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 379 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Gin.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which: the amino acid corresponding to or at position 350 is Met, and the amino acid corresponding to or at position 318 is Arg.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 350 is Met
  • amino acid corresponding to or at position 318 is Gly
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 350 is Met
  • amino acid corresponding to or at position 318 is Arg
  • amino acid corresponding to or at position 317 is Asn.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 210 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 317 is His
  • amino acid corresponding to or at position 318 is Gly
  • amino acid corresponding to or at position 345 is Gin.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 317 is Met
  • the amino acid corresponding to or at position 318 is Gly
  • the amino acid corresponding to or at position 345 is Gin.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 363 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred lie.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 419 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 249 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 247 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 407 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 306 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Lys.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 30 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 54 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 57 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 84 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 212 is Ala, Arg, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 223 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 243 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 264 is Ala, Arg, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 291 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which: the amino acid corresponding to or at position 327 is Ala, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 331 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 342 is Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 373 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 374 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 410 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 412 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 414 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 421 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 422 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Val.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 251 is Ala
  • the amino acid corresponding to or at position 405 is Asp.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 327 is Gly
  • amino acid corresponding to or at position 421 is Asp.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • the amino acid corresponding to or at position 251 is Ala
  • the amino acid corresponding to or at position 306 is Arg
  • the amino acid corresponding to or at position 317 is Leu
  • the amino acid corresponding to or at position 318 is Pro
  • the amino acid corresponding to or at position 321 is Pro
  • the amino acid corresponding to or at position 331 is Glu
  • the ami- no acid corresponding to or at position 350 is Met.
  • the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
  • amino acid corresponding to or at position 407 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
  • the encoded protein can be expressed recombinantly and the activity of the protein can be determined using, for example, assays described herein.
  • amino acids corresponding to the amino acids listed in Table 4a and 4b, 4c, and 4d can be chosen to be substituted by any other amino acid by conserved amino acids, and more preferably by the amino acids of tables 4a and 4b, 4c, and 4d.
  • Crop plants for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (muta- genesis).
  • Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady ® (glypho- sate) and Liberty Link ® (glufosinate) have been generated with the aid of genetic engineering methods.
  • crop plants also includes plants which, with the aid of genetic en- gineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp.
  • Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B.
  • thuringiensis such as the endotoxins CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 , Cry9c, Cry34Ab1 or Cry35Ab1 ; or vegetative insec- ticidal proteins (VIPs), for example VI P1 , VI P2, VI P3, or VIP3A; insecticidal proteins of nema- tode-colonizing bacteria, for example Photorhabdus spp.
  • VIPs vegetative insec- ticidal proteins
  • toxins of animal organisms for example wasp, spider or scorpion toxins
  • fungal toxins for example from Strep- tomycetes
  • plant lectins for example from peas or barley
  • agglutinins proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribo- some-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin
  • steroid-metabolizing enzymes for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase
  • ion channel blockers for example inhibitors of sodium channels or calcium channels
  • receptors of the group consisting of sodium channels or calcium channels for example
  • 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 pro- prise 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 en- gineering, 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 Solarium bulbocastanum ) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amy!vora).
  • PR proteins pathogenesis-related proteins
  • resistance proteins for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solarium bulbocastanum
  • T4 lysozyme for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amy!vora.
  • crop plants also includes plants whose productivity has been im- proved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
  • potential yield for example biomass, grain yield, starch, oil or protein content
  • tolerance to drought for example drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
  • crop plants also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for ex- ample by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsatu- rated omega 9 fatty acids (for example Nexera ® oilseed rape).
  • crop plants also includes plants which have been modified with the aid of ge- netic engineering methods for improving the production of raw materials, for example by in- creasing the amylopectin content of potatoes (Amflora ® potato).
  • the compounds of formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • compositions for the desiccation and/or defoliation of plants processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.
  • the compounds of formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • the compounds according to the invention, the N-oxides or agriculturally suitable salts thereof are used for controlling at least one of the following undesired plants: Alopecurus myosuroiedes, Echinocloa crus-galli, Amaranthus retroflexus, Chenopodium album.
  • the compounds of formula I, or the herbicidal compositions comprising the compounds of formula I can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed.
  • the use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.
  • the herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.
  • auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.
  • thickeners i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion
  • polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).
  • antifoams examples include silicone emulsions (such as, for example, Silikon ® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides can be added for stabilizing the aqueous herbicidal formulation.
  • bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.l. Pigment Red 112 and C.l. Solvent Red 1 , and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • Suitable inert auxiliaries are, for example, the following:
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
  • paraffin tetrahydronaphthalene
  • alkylated naphthalenes and their derivatives alkylated benzenes and their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclohexanone or strongly polar
  • Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea
  • Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g.
  • methylcellulose methylcellulose
  • hydrophobically modified starches polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the compounds of formula I or la, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
  • concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
  • concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges.
  • the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound.
  • the active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.
  • the compounds of formula I of the invention can for example be formulated as follows:
  • active compound 10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent.
  • wetters or other adjuvants are added.
  • the active corn- pound dissolves upon dilution with water. This gives a formulation with an active compound con- tent of 10% by weight.
  • active compound 15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion.
  • the formula- tion has an active compound content of 15% by weight.
  • active compound 25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • organic solvent e.g. alkylaromatics
  • calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight.
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Di- lution with water gives an emulsion.
  • the formulation has an active compound content of 25% by weight.
  • active compound 20 parts by weight of active compound are comminuted with addi- tion of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an or- ganic solvent to give a fine active compound suspension. Dilution with water gives a stable sus- pension of the active compound.
  • the active compound content in the formulation is 20% by weight.
  • active compound 50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
  • the formulation has an ac- tive compound content of 50% by weight.
  • active compound 75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable disper- sion or solution of the active compound.
  • the active compound content of the formulation is 75% by weight.
  • J. Granules 0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.
  • the compounds of formula I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • the compounds of formula I or the herbicidal compositions can be applied by treating seed.
  • the treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multi- layer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula I according to the invention or the compositions prepared therefrom.
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multi- layer coating, seed encrusting, seed dripping and seed pelleting
  • the herbicid- al compositions can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tu- bers, cuttings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • the rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
  • the compounds of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • Safeners are chemical compounds which prevent or reduce damage to useful plants without substantially affecting the herbicidal action of the compounds of formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cut- tings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of formula I can be used simultaneously or in succession.
  • Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1 H- 1 ,2,4-triazole-3-carboxylic acids, 1 -phenyl-4, 5-d i hyd ro-5-a I ky I- 1 A pyrazole-S ⁇ -dicarboxylic ac- ids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha- oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4- (aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5- thiazolecarboxylic acids, phosphoroth
  • the compounds of the formula I can be mixed and/or jointly applied with numerous representatives of other herbicidal or growth-regulating groups of active compounds or with safeners.
  • Suitable mixing partners are, for example, 1 ,2,4-thiadiazoles, 1 ,3,4-thiadiazoles, amides, aminophosphoric acid and its deriv- atives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, ben- zoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1 ,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivates, di
  • herbicides which can be used in combination with the benzamide compounds of formula I according to the present invention are:
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, bu- tafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulf
  • glyphosate glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);
  • bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;
  • amiprophos amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlor- propham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;
  • acetochlor alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dime- thenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor;
  • Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset, which radicals may be substituted by one to three groups R aa ; R 21 ,R 22 ,R 23 ,R 24 are H, halogen or Ci-C4-alkyl; X is O or NH; n is 0 or 1 .
  • R 21 ,R 22 ,R 23 ,R 24 are H, Cl, F or CH 3 ;
  • R 25 is halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl;
  • R 26 is CrC 4 - alkyl;
  • R 27 is halogen, Ci-C 4 -alkoxy or Ci-C 4 -haloalkoxy;
  • R 28 is H, halogen, Ci-C 4 -alkyl, Ci-C 4 - haloalkyl or Ci-C 4 -haloalkoxy;
  • m is 0, 1 , 2 or 3;
  • X is oxygen;
  • n is 0 or 1 .
  • Preferred compounds of the formula 2 have the following meanings:
  • R 21 is H; R 22 ,R 23 are F; R 24 is H or F; X is oxygen; n is 0 or 1 .
  • Particularly preferred compounds of the formula 2 are:
  • auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;
  • Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfa- mide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furi- lazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1- oxa-4-azaspiro[4.5]decane (H-1 1 ; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl)-l ,3-oxazolidine (H-12; R-29148, CAS 52836-31-4).
  • the active compounds of groups b1 ) to b15) and the safeners C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names
  • the invention also relates to compositions in the form of a crop protection composition formulated as a 1 -component composition
  • a crop protection composition formulated as a 1 -component composition
  • the invention also relates to compositions in the form of a crop protection composition formulat- ed as a 2-component composition
  • a first component comprising at least one corn- pound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound selected from the active corn- pounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where addi- tionally both components may also comprise further auxiliaries customary for crop protection compositions.
  • the weight ratio of the active compounds A:B is generally in the range of from 1 : 1000 to 1000: 1 , preferably in the range of from 1 :500 to 500: 1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
  • the weight ratio of the active compounds A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
  • the relative parts by weight of the components A:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 ;
  • the weight ratio of the components A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 ;
  • the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and
  • the weight ratio of the components A + B to the component C is in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
  • compositions according to the invention comprising in each case one individualized compound of the formula I and one mixing partner or a mixing partner combination are given in Table B below.
  • a further aspect of the invention relates to the compositions B-1 to B-1236 listed in Table B below, where in each case one row of Table B corresponds to a herbicidal composition corn- prising one of the compounds of formula I individualized in the above description (component 1 ) and the further active compound from groups b1) to b15) and/or safener C stated in each case in the row in question (component 2).
  • the active compounds in the compositions described are in each case preferably present in synergistically effective amounts.
  • the compounds of formula I and the compositions according to the invention may also have a plant-strengthening action. Accordingly, they are suitable for mobilizing the defense sys- tem of the plants against attack by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria.
  • Plant-strengthening (resistance-inducing) substances are to be under- stood as meaning, in the present context, those substances which are capable of stimulating the defense system of treated plants in such a way that, when subsequently inoculated by un- wanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms.
  • the compounds of formula I can be employed for protecting plants against attack by un- wanted microorganisms within a certain period of time after the treatment.
  • the period of time within which their protection is effected generally extends from 1 to 28 days, preferably from 1 to 14 days, after the treatment of the plants with the compounds of formula I, or, after treatment of the seed, for up to 9 months after sowing.
  • the compounds of formula I and the compositions according to the invention are also suitable for increasing the harvest yield.
  • HPLC-MS high performance liquid chromatography coupled with mass spectrometry;
  • HPLC column 15 RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50 * 4.6 mm;
  • mobile phase acetonitrile + 0.1 % trifluoroacetic acid (TFA)/water + 0.1 % TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40'C, flow rate 1.8 ml/min.
  • Step 4 3-Benzyloxy-2,4-dichloro-6-fluoro-N-(1 -methyltetrazol-5-yl)-benzamide
  • the suspension was diluted with an additional 100 ml of THF, warmed up to 25°C, stirred overnight and then quenched with 1 10 ml of 2 N hydrochloric acid
  • the organic phase was washed three times with 20 ml of 2 N hydrochloric acid and once with 20 ml brine.
  • the organic phase was dried over Na 2 S0 4 and evaporated to yield 46.5 g of the product as a pale white solid.
  • Step 6 [2,4-Dichloro-N-(1 -methyltetrazol-5-yl)-3-[2-oxo-2-(2,2,2-trifluoroethylamino)-ethoxy]- benzamide
  • # denotes the attachment point to the oxygen atom.
  • the culture containers used were plastic flowerpots containing loamy sand with approxi- mately 3.0% of humus as the substrate.
  • the seeds of the test plants were sown separately for each species.
  • the active ingredients which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles.
  • the containers were irrigated gently to promote germination and growth and subsequently cov- ered with transparent plastic hoods until the plants had rooted. This cover caused uniform ger- mination of the test plants, unless this had been impaired by the active ingredients.
  • test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water.
  • the test plants were either sown di- rectly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • the plants were kept at 10 - 25°C or 20 - 25°C, respectively.
  • the test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

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Abstract

La présente invention concerne des composés benzamide de formule I (I), dans laquelle les variables sont définies comme dans les revendications et la description, les N-oxydes et les sels de ceux-ci, et des compositions les comprenant. L'invention concerne également l'utilisation des composés benzamide ou des compositions comprenant de tels composés pour lutter contre la végétation indésirable, et un procédé de lutte contre la végétation indésirable par l'application desdits composés ou compositions.
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US20200331866A1 (en) * 2018-01-08 2020-10-22 Basf Se Benzamide compounds and their use as herbicides

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