WO2016034352A1 - Utilisation de composés de n-thio-anthranilamide sur des plantes cultivées - Google Patents

Utilisation de composés de n-thio-anthranilamide sur des plantes cultivées Download PDF

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WO2016034352A1
WO2016034352A1 PCT/EP2015/068006 EP2015068006W WO2016034352A1 WO 2016034352 A1 WO2016034352 A1 WO 2016034352A1 EP 2015068006 W EP2015068006 W EP 2015068006W WO 2016034352 A1 WO2016034352 A1 WO 2016034352A1
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plant
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plants
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William Baxter
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BASF SE
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to a method for controlling pests and/or increasing the plant health of a cultivated plant with at least one modification (hereinafter abbreviated as "cultivated plant”) as compared to the respective non-modified control plant, comprising the application of a pesti- cidally active compound of formula I
  • R 1 is selected from the group consisting of H, F, CI, Br and CN;
  • R 2 is selected from the group consisting of F, CI, Br, I, CH3;
  • R 3 is selected from the group consisting of Br, CI, CHF2, CF3 and OCH2F;
  • R 4 is CI or CF 3 ;
  • R 5 , R 6 are selected independently of one another from the group consisting of hydrogen, Ci-C4-alkyl, Cs-Cs-cycloalkyl, or
  • R 5 and R 6 together represent a C2-C7-alkylene, C2-C7-alkenylene or
  • k O or l ;
  • compound of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof is un- derstood to include a polymorphic crystalline form, a co-crystal or a solvate of a compound or a stereoisomer, salt, tautomer or N-oxide, even if not mentioned explicitly.
  • plant health comprises various sorts of improvements of plants that are not connected to the control of pests and which do not embrace the reduction of negative conse- quences of harmful insects.
  • plant health is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e.g.
  • plant vigor e.g. improved plant growth and/or greener leaves ("greening effect")
  • quality e.g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e.g. improved biomass and/or increased content of valuable ingredients
  • plant vigor e.g. improved plant growth and/or greener leaves ("greening effect")
  • quality e.g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e.g. improved content or composition of certain ingredients
  • cultivated plants are plants that have at least one insecticidal trait. It is a wide-spread problem that insects, that are combatted with insectides, develop resistance, i.e. they become less or not all anymore susceptible to the insecticidal effect.
  • compounds of formula (I) are useful in methods of controlling harmful insects by treating cultivated plants, parts of such plants or their locus of growth, wherein the plant has at least one insecticidal trait, and wherein the harmful insects are resistant to an insecticidal trait of the plant.
  • cultivated plants are specific plants that have at least one herbicidal and at least one insecticidal trait, preferably soybeans, more preferably the soybeans known as"lntacta RR2 PRO" soybean (Monsanto).
  • soybeans more preferably the soybeans known as"lntacta RR2 PRO" soybean (Monsanto).
  • compounds of formula (I) are also useful in methods of controlling harmful insects by treating those mentioned cultivated plants, parts of such plants or their locus of growth.
  • cultivated plants are plants that have at least one trait or trait
  • WO2007/006670, WO2013/024009, WO2013/024010 and WO2013/174645 describe N-thio- anthranilamide compounds with a sulfilimine or sulfoximine group and their use as pesticides.
  • WO2014/053395 describes the use of N-thio-anthranilamide compounds on certain cultivated plants.
  • the compounds of formula (I) can be prepared according to standard methods of organic chemistry, or by the processes as described in WO2013/024007, WO2013/024008, WO2013/076092, and the unpublished applications PCT/EP2014/056164, EP13173044.2, PCT/EP2014/060082, and EP14166089.4 d, without being limited to the routes given therein.
  • the preparation of the compounds of formula I above may lead to them being obtained as isomer mixtures. If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.
  • Agronomically acceptable salts of the compounds I can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
  • anthranilamide compounds of formula (I) themselves have been described in methods and uses for controlling harmful pests on certain cultivated plants, there are further cultivated plants on which the compounds of formula (I) are surprisingly effective.
  • the compounds of formula (I) as well as the terms "compounds for methods according to the (present) invention”, “compounds according to the (present) invention” or “compounds of formula (I)” or “compound(s) II", which all compound(s) are applied in methods and uses according to the present invention comprise the compound(s) as defined herein as well as a known stereoisomer, salt, tautomer or N-oxide thereof (including a polymorphic crystalline form, a co-crystal or a solvate of a compound or a stereoisomer, salt, tautomer or N-oxide thereof).
  • composition(s) according to the invention or “composition(s) of the present invention” encompasses composition(s) comprising at least one compound of formula (I) or mixtures of the compounds of formula (I) with other pesticidally active compound(s) II for being used and/or applied in methods according to the invention as defined above.
  • the compounds of the 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 the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double- bond, nitrogen-sulfur double bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • Salts of the compounds of the present invention are preferably agriculturally and veterinarily acceptable 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.
  • suitable "agriculturally useful salts” or “agriculturally acceptable salts” are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci- C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise me- thylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trime- thylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sul- fonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4- alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • N- oxide includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N-oxides of compounds (I) can in particular be prepared by oxidizing the ring nitrogen atom(s) of the pyridine ring and/or the pyrazole ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides. The person skilled in the art knows if and in which positions compounds of the formula (I) of the present invention may form N-oxides.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of formula (I), their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula (I), its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • co-crystal denotes a complex of the compounds according to the invention or a ste- reoisomer, salt, tautomer or N-oxide thereof, with one or more other molecules (preferably one molecule type), wherein usually the ratio of the compound according to the invention and the other molecule is a stoichiometric ratio.
  • solvate denotes a co-complex of the compounds according to the invention, or a stereoisomer, salt, tautomer or N-oxide thereof, with solvent molecules.
  • the solvent is usually liquid. Examples of solvents are methanol, ethanol, toluol, xylol.
  • a preferred solvent which forms solvates is water, which solvates are referred to as "hydrates".
  • a solvate or hydrate is usually characterized by the presence of a fixed number of n molecules solvent per m molecules compound according to the invention.
  • 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.
  • partially or fully halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • a partially or fully halogenated radical is termed below also "halo- radical”.
  • partially or fully halogenated alkyl is also termed haloalkyl.
  • alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyi) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 6 or 1 to 4 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
  • Ci-C4-alkyl examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (sec-butyl), isobutyl and tert- butyl.
  • Ci-C6-alkyl are, apart those mentioned for Ci-C4-alkyl, n-pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, n-hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2- trimethylpropyl, 1 -ethyl-1 -methyl
  • alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • cycloalkyl as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicy-hack cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C3-Cio-cycloalkyl”), preferably 3 to 8 carbon atoms (“Cs-Cs-cycloalkyl”) or in particular 3 to 6 carbon atoms (“C3-C6- cycloalkyl").
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicy- clo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicy- clo[3.2.1 ]octyl.
  • alkenyl denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 7 carbon atoms (“C2-C7-alkenyl”), in particular 2 to 4 carbon atoms (“C2-C4-alkenyl”), and a double bond in any position, for example C2-C4- alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1-methylethenyl, 1 -butenyl, 2-butenyl, 3- butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3- butenyl, 1
  • alkenylene (or alkenediyl) as used herein in each case denotes an alkenyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • alkynyl denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 10 (“C2-Cio-alkynyl”), frequently 2 to 6 (“C2-C6-alkynyl”), preferably 2 to 4 carbon atoms (“C2-C4-alkynyl”) and one or two triple bonds in any position, for example C2- C4-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl
  • alkynylene (or alkynediyl) as used herein in each case denotes an alkynyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • alkoxy denotes in each case a straight-chain or branched alkyl group usually having usually froml to 4 carbon atoms ("Ci-C4-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C4-Alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy).
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1 - dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 - methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2- dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,
  • alkoxyalkyl denotes in each case alkyl usually comprising 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 4 carbon atoms as defined above.
  • Ci-C4-Alkoxy-Ci-C6-alkyl is a Ci-C4-alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Examples are CH2OCH3, CH2-OC2H5, n-propoxymethyl, CH 2 -OCH(CH 3 )2, n-butoxymethyl, (1 -methylpropoxy)- methyl, (2-methylpropoxy)methyl, CH 2 -OC(CH 3 )3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n- propoxy)-ethyl, 2-(1 -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2- methylpropoxy)-ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n- propoxy)-propyl, 2-(1 -methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1 -methylpropoxy)-prop
  • alkylsulfinyl and S(0) n -alkyl (wherein n is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • alkylsulfinyl and “S(0) n -alkyl” (wherein n is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Si-C2-a I kylsu If i nyl refers to a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl refers to a Ci-C4-alkyl group, as defined above, at- tached via a sulfinyl [S(O)] group.
  • Ci-C6-alkylsulfinyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C2-alkylsulfinyl is methylsulfinyl or ethyl- sulfinyl.
  • Ci-C4-alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl).
  • Ci-C6-alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl,
  • alkylsulfonyl and “S(0) n -alkyl” are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • C1-C2- alkylsulfonyl refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C4-alkylsulfonyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C6-alkylsulfonyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-alkylsulfonyl is methylsulfonyl or ethyl- sulfonyl.
  • Ci-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2- methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl).
  • C1-C6- alkylsulfonyl is additionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl, 2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2- dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 - methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1 ,1 -dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1 ,3-dimethylbutylsul
  • aryl refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.
  • heteroaryl refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrimidyl and the like.
  • a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, is a ring system wherein two oxygen atoms must not be in adjacent positions and wherein at least 1 carbon atom must be in the ring system e.g.
  • a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur also is e.g.
  • a saturated, partially unsaturated or unsaturated 5-or 6-membered heterocycle which contains 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur, such as pyridine, pyrimidine,
  • a saturated, partially unsaturated or unsaturated 5-or 6-membered heterocycle which contains 1 nitrogen atom and 0 to 2 further heteroatoms selected from oxygen, nitrogen and sulfur, preferably from oxygen and nitrogen, such as piperidine, piperazin and morpholine.
  • this ring system is a saturated, partially unsaturated or unsaturated 3- to 6- membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sul- fur, wherein two oxygen atoms must not be in adjacent positions and wherein at least 1 carbon atom must be in the ring system.
  • this ring system is a radical of pyridine, pyrimidine, (1 ,2,4)-oxadiazole, 1 ,3,4- oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1 ,2,4- triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane or oxetane.
  • the compounds of formula (I) can be prepared according to standard methods of organic chemistry, or by the processes as described in WO2013/024007, WO2013/024008, WO2013/076092, and the unpublished applications PCT/EP2014/056164, EP13173044.2, PCT/EP2014/060082, and EP14166089.4 d, without being limited to the routes given therein.
  • Agronomically acceptable salts of the compounds I can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
  • R 1 is selected from the group consisting of CI, Br and CN.
  • R 1 is CI.
  • R 1 is CN
  • R 2 is selected from the group consisting of CI, Br and CH3 (Me).
  • R 2 is CI
  • R 2 is CH3.
  • the invention relates to methods and uses, in which in the compound of formula I
  • R 1 is selected from the group consisting of Br, CI, CN, preferably CI;
  • R 2 is selected from the group consisting of CI, CH3; preferably CH3.
  • R 1 is CI
  • R 2 is CH3.
  • R 1 is CI
  • R 2 is CI
  • R 1 is CN
  • R 2 is CH3.
  • k is 0 in the compounds of formula (I):
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are as defined herein.
  • k is 1 in the compounds of formula (I):
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are as defined herein.
  • the invention relates to methods and uses, in which in the compound of formula I
  • R 3 is CF3 or Br, preferably CF3.
  • R 4 is CI.
  • the invention relates to methods and uses, in which in the compound of formula I
  • R 1 is selected from the group consisting of Br, CI, CN, preferably CI;
  • R 2 is selected from the group consisting of CI, CH3; preferably CH3;
  • R 3 is CF3 or Br, preferably CF3;
  • R 4 is CI.
  • the invention relates to methods and uses of compounds of formula (I), in which R 5 and R 6 are selected independently of one another from the group consisting of hydrogen, Ci-C4-alkyl and Cs-Cs-cycloalkyl.
  • the invention relates to methods and uses of compounds of formula (I), in which R 5 and R 6 are selected from Ci-C4-alkyl, preferably selected from methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropylmethyl, preferably selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, more preferably methyl, ethyl, isopropyl, most preferably ethyl.
  • R 5 and R 6 are selected from Ci-C4-alkyl, preferably selected from methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropylmethyl, preferably selected from methyl, ethyl, n-prop
  • the invention relates to methods and uses of compounds of formula (IB), in which R 5 and R 6 are selected from methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropylmethyl, preferably methyl, ethyl, isopropyl, most preferably ethyl.
  • the invention relates to methods and uses of compounds of formula (IC), in which R 5 and R 6 are selected from methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropylmethyl, preferably methyl, ethyl, isopropyl, most preferably ethyl.
  • R 5 and R 6 are selected from methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropylmethyl, preferably methyl, ethyl, isopropyl, most preferably ethyl.
  • the invention relates to methods and uses of compounds of formula (ID), in which R 5 and R 6 are selected from methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropylmethyl, preferably methyl, ethyl, isopropyl, most preferably ethyl.
  • R 5 and R 6 together represent a C2-C7-alkylene, C2-C7-alkenylene or C6-Cg-alkynylene chain forming together with the sulfur atom to which they are attached a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or fully unsaturated ring.
  • R 5 and R 6 are identical, and preferably selected from methyl, ethyl, and isopropyl.
  • a group of especially preferred compounds of formula I in the methods and uses according to the invention are compounds 1-1 to I-82 of formula IA which are listed in the table A.
  • a compound selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 as in Ta ble A' is the compound I in the methods and uses according to the invention.
  • a compound selected from compounds I-52, I-57, I-62, I-67, I-72 as i Table A" is the compound I in the methods and uses according to the invention.
  • 1-1 1 is the compound I in the methods and uses according to the invention
  • 1-16 is the compound I in the methods and uses according to the invention
  • 1-21 is the compound I in the methods and uses according to the invention
  • I-26 is the compound I in the methods and uses according to the invention
  • 1-31 is the compound I in the methods and uses according to the invention.
  • R 1 , R 2 , R 3 , R 4 are as defined herein and are preferably ⁇ -1 or ⁇ -2.
  • the compounds of formula I are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:
  • insects from the order of Lepidoptera for example Achroia grisella, Acleris spp. such as A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A.
  • Argyresthia conjugel- la Argyroploce spp., Argyrotaenia spp.
  • A. velutinana Athetis mindara, Austroasca vi- ridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bon- agota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C.
  • Cactoblastis cactorum Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilo spp. such as C. Indi- cus, C. suppressalis, C. partellus; Choreutis pariana, Choristoneura spp. such as C. conflictana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C.
  • kuehniella kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. such as F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G. molesta, G.
  • H. armigera Heliothis armigera
  • H. zea Heliothis zea
  • Heliothis spp. such as H. assulta, H. subflexa, H. virescens
  • Hellula spp. such as H. undalis, H.
  • Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quin- quemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mods spp. such as M. lapites, M.
  • operculella Phyllocnistis citrella, Phyllonorycter spp. such as P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathy- pena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P.
  • insects from the order of Coleoptera for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. planipennis, A. sinuatus; Agriotes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimal- lus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala diveren- ta, Anomala rufocuprea, Anoplophora spp. such as A.
  • Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogo- nia spp., Athous haemorrhoidalis, Atomaria spp. such as A. linearis; Attagenus spp., Aula- cophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B.
  • vespertinus Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryp- torhynchus lapathi, Ctenicera spp. such as C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D.
  • Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestis, E. vigintioctomaculata; Epitrix spp. such as E. hirtipennis, E.
  • hypomeces squamosus Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lath- ridius spp., Lema spp. such as L. bilineata, L. melanopus; Leptinotarsa spp. such as L. decem- lineata; Leptispa pygmaea, Limonius califomicus, Lissorhoptrus oryzophilus, Lixus spp., Lu- perodes spp., Lyctus spp. such as L.
  • Saperda Candida Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobium paniceum, Stemechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. such as T.
  • Trogoderma spp. Tychius spp.
  • Xylotrechus spp. such as X. pyrrhoderus
  • Za- brus spp. such as Z. tenebrioides
  • insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A. sinensis; Bac- trocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capi- tata, Chrysomyia spp. such as C.
  • Aedes spp. such as A. aegypti, A. albopictus, A. vexans
  • Anastrepha ludens Anopheles spp.
  • A. albimanus such as A.
  • insects from the order of Thysanoptera for example, Basothrips biformis, Dichromothrips cor- betti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S.
  • insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hilare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsu- gae, Adelphocoris spp., such as A. rapidus, A.
  • Diaspis spp. such as D. bromeliae; Dichelops eatus, Diconoco- ris hewetti, Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp. such as D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. such as D. cingulatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. such as E.
  • Idiocerus spp. Idioscopus spp., Laodelphax striatellus, Lecani- um spp., Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Leptocorisa spp., Lep- toglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L. hesperus, L. lineolaris, L.
  • Nasonovia ribis-nigri Nasonovia ribis-nigri, Neotoxoptera formosana, Neomegalotomus spp, Nephotettix spp. such as N. malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. such as N. viridula; Nilaparvata lugens, Nysius huttoni, Oebalus spp. such as O.
  • Pteromalus spp. Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastro- coccus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R.
  • T. accerra, T. perditor Tibraca spp., Tomaspis spp., Toxoptera spp. such as T. aurantii; Trialeurodes spp. such as T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifolii,
  • Paravespula spp. such as P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P. megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polistes rubiginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, S.invicta, S.
  • Insects from the order Orthoptera for example Acheta domesticus, Calliptamus italicus, Chor- toicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria angulifera, Locusta spp. such as L. migratoria, L. pardalina; Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M.
  • Boophilus spp. such as B. annulatus, B. decoloratus, B. mi- croplus, Dermacentor spp. such as D.silvarum, D. andersoni, D. variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as /. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O.
  • Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R. sanguineus, R. appendiculatus, Rhipicephalus evertsi, Rhizoglyphus spp., Sarcoptes spp. such asS. Scabiei; and Family Eriophyidae including Aceria spp. such as A. sheldoni, A. anthocoptes, Acallitus spp., Aculops spp. such as A. lycopersici, A. pelekassi; Aculus spp.
  • Tetranychidae including Eotetranychus spp., Eute- tranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, ⁇ , pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychus spp. such as P. ulmi, P. citri; Metatetranychus spp. and Oligonychus spp. such as O. pratensis, O.
  • Pests from the Phylum Nematoda for example, plant parasitic nematodes such as root-knot nematodes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifolii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Aphelenchoides spp. such as A.
  • plant parasitic nematodes such as root-knot nematodes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. ros
  • Awl nematodes Dolichodorus spp.
  • Spiral nematodes Heliocotylenchus multicinctus
  • Sheath and sheathoid nematodes Hem- icycliophora spp. and Hemicriconemoides spp.
  • Hirshmanniella spp. Lance nematodes, Hop- loaimus spp.
  • False rootknot nematodes Nacobbus spp.
  • Needle nematodes Longidorus spp. such as L. elongatus
  • Lesion nematodes Pratylenchus spp. such as P.
  • brachyurus P. neglec- tus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform nematodes, Rotylenchus spp. such as R. robustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T. obtusus, T. primitivus; Paratrichodorus spp. such as P.
  • Stunt nematodes Tylencho- rhynchus spp. such as T. claytoni, T. dubius
  • Citrus nematodes Tylenchulus spp. such as T. semipenetrans
  • Dagger nematodes Xiphinema spp.
  • other plant parasitic nematode species such as T. claytoni, T. dubius
  • Neotermes spp. Procornitermes spp., Zootermopsis spp. such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. such as R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natalensis, Insects from the order Blattaria for example Blatta spp. such as B. orientalis, B. lateralis; Blat- tella spp. such as B. asahinae, B.
  • Thysanura for example Lepisma saccharina , Ctenolepisma urbana, and Thermobia domestica
  • Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera coleoptrata;
  • Pests from the class Diplopoda for example Blaniulus guttulatus, Julus spp., Narceus spp.
  • Pests from the class Symphyla for example Scutigerella immaculata
  • Insects from the order Collembola for example Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber,
  • Insects from the order Phthiraptera for example Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pediculus humanus corporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis; Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,
  • Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp.; class Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp
  • Haemonchus contortus such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesoph- agostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp.,
  • Taenia saginata Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichi- nella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
  • insects preferably sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera, and chewing-biting pests such as insects from the genera of Lepidoptera and Coleoptera, in particular the following species: Thysanoptera : Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips pa Imi and Thrips tabaci.
  • Mixtures of the present invention are particularly useful for controlling insects of the orders Lepidoptera, Coleoptera, Hemiptera and Thysanoptera.
  • the mixtures of the present invention are especially suitable for efficiently combating pests like insects from the order of the lepidopterans (Lepidoptera), beetles (Coleoptera), flies and mosquitoes (Diptera), thrips (Thysanoptera), termites (Isoptera), bugs, aphids, leafhoppers, white- flies, scale insects, cicadas (Hemiptera), ants, bees, wasps, sawflies (Hymenoptera), crickets, grasshoppers, locusts (Orthoptera), and also Arachnoidea, such as arachnids (Acarina).
  • the compounds of formula I are employed as a solo prod- uct.
  • the present invention also relates to methods for controlling pests and/or increasing the plant health of a cultivated plant, comprising in the application of a mixture of a compound of formula I and a pesticide II to a cultivated plant, parts of such plant, plant propagation material, or at its locus of growth.
  • the compounds of formula I are employed in combination (e.g. a mixture) with one or more compounds II which is a preferably a further in- secticide or a fungicide.
  • the pesticidally active compounds II with which the compounds of formula I are combined with for the methods according to present invention are the following:
  • the compound (II) pesticides, together with which the compounds of formula I may be used according to the purpose of the present invention, and with which potential synergistic effects with regard to the method of uses might be produced, are selected and grouped according to the Mode of Action Classification from the Insecticde Resistance Action Committee (IRAC) and are selected from group M consisting of
  • M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1 A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofu- ran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfen
  • GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S- cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fen
  • M.4 Nicotinic acetylcholine receptor agonists from the class of M.4A neonicotinoids, for example acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thia- cloprid and thiamethoxam; or the compounds M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'- nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1 -[(6-Chloropyridin-3-yl)methyl]-7- methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; or from the class M.4B nicotine;
  • M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin; M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues as hydroprene, ki- noprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
  • M.8 miscellaneous non-specific (multi-site) inhibitors for example M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
  • M.9 Selective homopteran feeding blockers for example M.9B pymetrozine, or M.9C floni- camid;
  • M.10 Mite growth inhibitors for example M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
  • M.1 1 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry-IAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase for example M.12A diafenthiuron, or M.12B or- ganotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetrad if on;
  • Nicotinic acetylcholine receptor (nAChR) channel blockers for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
  • benzoylureas as for example bistriflu- ron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novalu- ron, noviflumuron, teflubenzuron or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 as for example buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;
  • Octopamin receptor agonists as for example amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors for example M.20A hydramethyl- non, or M.20B acequinocyl, or M.20C fluacrypyrim;
  • M.21 Mitochondrial complex I electron transport inhibitors for example M.21 A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers for example M.22A indoxacarb, or M.22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4- chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid deriva- tives, for example spirodiclofen, spiromesifen or spirotetramat;
  • M.24 Mitochondrial complex IV electron transport inhibitors for example M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide; M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides as for example flubendia- mide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), tetraniliprole, or the phthalamide compounds M.28.1 : (R)-3-Chlor-N1 - ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluor-1 -
  • insecticidal active compounds of unknown or uncertain mode of action as for example afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, flu- ensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butox- ide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or the com- pounds
  • M.29.5 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or
  • M.29.6a (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2- trifluoro-acetamide
  • M.29.6b (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]- 2,2,2-trifluoro-acetamide
  • M.29.6c (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2- pyridylidene]acetamide
  • M.29.6d (E/Z)-N-[1 -[(6-bromo-3-pyridyl)methyl]-2
  • M.29.9.a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 - oxothietan-3-yl)benzamide; or M.29.9.b): fluxametamide; or
  • M.29.10 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; or a compound selected from the group of M.29.1 1 , wherein the compound is selected from M.29.1 1 b) to M.29.1 1 p): M.29.1 1.b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 , 2,2,3,3,3- hexafluoro-1 -(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.29.1 1.c) 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M.29.
  • M.29.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 , 2,3,5, 6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.29.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; or the compounds
  • M.29.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16c) N,5- dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide; M.29.16d) 1 - [1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
  • M.29.16e N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.29.16f 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.29.16h N-methyl-1 -(2-fluoro-1 -methyl-propyl]-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • M.29.16i 1 -(4,4-difluorocyclohexyl)-N-ethyl-5
  • M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j): M.29.17a) N-(1 - methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.29.17b) N-cyclopropyl-2-(3- pyridinyl)-2H-indazole-4-carboxamide; M.29.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4- carboxamide; M.29.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.29.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide;
  • M.29.171) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.29.17g) N- [(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.29.17h) N-(2,2- difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.29.17i) 2-(3-pyridinyl )-N-(2- pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.29.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2- (3-pyridinyl)-2H-indazole-5-carboxamide, or
  • M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d): M.29.18a) N-[3- chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide; M.29.18b) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide;
  • M.29.18c N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N- ethyl-propanamide; M.29.18d) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2- difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide; or the compound
  • the M.4 neonicotinoid cycloxaprid is known from WO2010/069266 and WO201 1/069456, the neonicotinoid M.4A.2, sometimes also to be named as guadipyr, is known from
  • WO2013/003977 and the neonicotinoid M.4A.3 (approved as paichongding in China) is known from WO2007/101369.
  • the metaflumizone analogue M.22B.1 is described in CN10171577 and the analogue M.22B.2 in CN102126994.
  • the phthalamides M.28.1 and M.28.2 are both known from WO2007/101540.
  • the anthranilamide M.28.3 is described in WO2005/077934.
  • the hydra- zide compound M.28.4 is described in WO2007/043677.
  • the anthranilamide M.28.5i) is de- scribed in WO201 1/085575, M.28.5j) in WO2008/134969, M.28.5k) in US201 1/046186 and
  • the diamide compound M.28.6 can be found in WO2012/034472.
  • the spiroketal-substituted cyclic ketoenol derivative M.29.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.29.4 from WO2008/06791 1.
  • the tri- azoylphenylsulfide M.29.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707.
  • the compounds M.29.6a) to M.29.6i) listed under M.29.6 are described in WO2012/029672, and M.29.6j) and M.29.6k) in
  • the nematicide M.29.8 is known from WO2013/055584.
  • the isoxazoline M.29.9.a) is described in WO2013/050317.
  • the isoxazoline M.29.9.b) is described in
  • the pyridalyl-type analogue M.29.10 is known from WO2010/060379.
  • the carboxamides broflanilide and M.29.1 1.b) to M.29.1 1.h) are described in WO2010/018714, and the carboxamides M.29.1 1 i) to M.29.1 1.p) in WO2010/127926.
  • the pyridylthiazoles M.29.12.a) to M.29.12.C) are known from WO2010/006713, M.29.12.d) and M.29.12.e) are known from WO2012/000896, and M.29.12.f) to M.29.12.m) from WO2010/129497.
  • the compounds M.29.14a) and M.29.14b) are known from WO2007/101369.
  • the pyrazoles M.29.16.a) to M.29.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, respectively, and the pyrazoles M.29.16i) and M.29.16j) are described in US 61/891437.
  • the pyridinyl- indazoles M.29.17a) to M.29.17.j) are described in WO2015/038503.
  • the pyridylpyrazoles M.29.18a) to M.29.18d) are described in US2014/0213448.
  • the isoxazoline M.29.19 is described in WO2014/036056.
  • the isoxazoline M.29.20 is known from WO2014/090918.
  • a compound of formula (I) in mixture with fipronil is applied, preferably in the methods for seed treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the plant propagation material of the cultivated plant, preferably seeds, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'
  • a compound of formula (I) in mixture with ethiprole is applied, preferably in the methods for seed treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the plant propagation material of the cultivated plant, preferably seeds wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with chlorfenapyr is applied, preferably in the methods for foliar treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the cultivated plant, parts of the cultivated plant or to their habitat, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with teflubenzuron is applied, preferably in the methods for foliar treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the cultivated plant, parts of the cultivated plant or to their habitat, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with chlorfenapyr and teflubenzuron is applied, preferably in the methods for foliar treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the cultivated plant, parts of the cultivated plant or to their habitat, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with dinotefuran is applied, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with chlorantraniliprole is applied, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with cyantraniliprole is applied, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with pyrethroids, preferably alpha-cypermethrin, is applied, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • the pesticide II is selected from the group of fipronil, alpha-cypermethrin, dinotefuran, chlorfenapyr, teflubenzuron and sulfoxaflor.
  • a compound II selected from group M.2 GABA-gated chloride channel antagonists as defined above is preferred, in particular group M.2B (fiproles), especially preferred ethiprole and fipronil.
  • a compound II selected from group M.3 (Sodium channel modulators) as defined above is preferred, in particular group M.3A (pyrethroids), especially preferred alpha-cypermethrin and cyhalothrin.
  • group M.3A pyrethroids
  • alpha-cypermethrin cyhalothrin.
  • a compound II selected from group M.4A (Neonicotinoids) as defined above is preferred, in particular clothianidin, dinotefuran, imidacloprid, thiacloprid, or thiamethoxam.
  • Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A or Table A", with clothianidin as compound II are also preferred. Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with dinotefuran as compound II are also preferred. Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with imidacloprid as compound II are also preferred. Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A or Table A", with thiacloprid as compound II are also preferred. Mixtures of compounds of formula I with sulfoxaflor as compound II are also preferred.
  • the compound II is selected from group M.5 (Nicotinic acetylcholine receptor allosteric activators) and is preferably spinosad or spinetoram.
  • the compound II is selected from group M.6 (Chloride channel activators) and is preferably an avermectin.
  • the compound II is selected from group M.9 (Selective homopteran feeding blockers) and is preferably pymetrozine or flonicamid. Mixtures of compounds of formu- la I as individualized herein, e.g. in Table A, Table A' or Table A", with pymetrozine as compound II are especially preferred. Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with flonicamid as compound II are especially preferred.
  • the compound II is selected from group M.13 (Uncouplers of oxidative phosphorylation via disruption of the proton gradient) and is preferably chlorfenapyr.
  • group M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient
  • chlorfenapyr Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with chlorfenapyr as compound II are especially preferred.
  • the compound II is selected from group M.16 (Inhibitors of the chitin biosynthesis type 1 ) and is preferably buprofezin.
  • the compound II is selected from group M.22 (Voltage-dependent sodium channel blockers) and is preferably metaflumizone.
  • the compound II is selected from group M.23 (Inhibitors of the of acetyl CoA carboxylase) and is preferably a Tetronic or Tetramic acid derivative, spirodiclofen, spi- romesifen or spirotetramat.
  • Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A or Table A", with Tetronic Acid as compound II are preferred. Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with Tetramic Acid as compound II are also preferred. Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with Tetramic Acid as compound II are also preferred.
  • the compound II is selected from group M.26 (Ryanodine receptor- modulators) and is preferably chlorantraniliprole or cyantraniliprole.
  • Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with chlorantraniliprole as compound II are especially preferred.
  • Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with cyantraniliprole as compound II are especially preferred.
  • the compound II is sulfoxaflor.
  • Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with sulfoxaflor as compound II are especially preferred.
  • the compound (II) pesticides are selected from fungicides.
  • the following list of fungicides, in conjunction with which the com- pounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:
  • Inhibitors of complex III at Q 0 site e. g. strobilurins: azoxystrobin (A.1 .1 ), coumethoxy- strobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1.5), fenamin- strobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.1 1 ), orysastrobin (A.1.12), picoxy.strobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1 .16), tri- floxystrobin (A.1 .17), 2-(2-
  • inhibitors of complex II e. g. carboxamides: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobiphenyl-2-yl)-
  • respiration inhibitors e. g. complex I, uncouplers: diflumetorim (A.4.1 ), (5,8-difluoro- quinazolin-4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine (A.4.2); nitrophenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); and silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides)
  • SBI fungicides Sterol biosynthesis inhibitors
  • C14 demethylase inhibitors (DMI fungicides): triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1 .4), difenoconazole (B.1 .5), diniconazole (B.1.6), diniconazole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1 .9), fluquinconazole (B.1.10), flusilazole (B.1 .1 1 ), flutriafol (B.1 .12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclo
  • Delta14-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox- amine (B.2.8);
  • Inhibitors of 3-keto reductase fenhexamid (B.3.1 );
  • phenylamides or acyl amino acid fungicides benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiral- axyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (mefenoxam, C.1 .5), ofurace (C.1 .6), oxadixyl (C.1.7); others: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4- fluorophenylmethoxy)pyrimidin-4-amine (C.2.7);
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl (D1.1 ), carbendazim (D1.2), fuberidazole (D1.3), thiabendazole (D1 .4), thiophanate-methyl (D1.5); triazolopyrim- idines: 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]tri- azolo[1 ,5-a]pyrimidine (D1 .6);
  • diethofencarb (D2.1 ), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);
  • methionine synthesis inhibitors anilino-pyrimidines: cyprodinil (E.1 .1 ), mepanipyrim (E.1.2), pyrimethanil (E.1 .3);
  • blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hy- drochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine (E.2.7), validamycin A (E.2.8);
  • MAP / histidine kinase inhibitors fluoroimid (F.1 .1 ), iprodione (F.1 .2), procymidone (F.1 .3), vinclozolin (F.1 .4), fenpiclonil (F.1 .5), fludioxonil (F.1.6);
  • quinoxyfen F.2.1 ;
  • Phospholipid biosynthesis inhibitors edifenphos (G.1.1 ), iprobenfos (G.1 .2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);
  • lipid peroxidation dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
  • phospholipid biosynthesis and cell wall deposition dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7) and N-(1 -(1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4- fluorophenyl) ester (G.3.8);
  • inorganic active substances Bordeaux mixture (H.1.1 ), copper acetate (H.1 .2), copper hydroxide (H.1.3), copper oxychloride (H.1 .4), basic copper sulfate (H.1.5), sulfur (H.1 .6);
  • thio- and dithiocarbamates ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 ), N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide (H.3.12);
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles
  • guanidines and others guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);
  • inhibitors of glucan synthesis validamycin (1.1 .1 ), polyoxin B (1.1 .2);
  • melanin synthesis inhibitors pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (1.2.3), di- cyclomet (I.2.4), fenoxanil (I.2.5);
  • acibenzolar-S-methyl J.1.1
  • probenazole J.1.2
  • isotianil J.1 .3
  • tiadinil J.1 .4
  • prohexa- dione-calcium J.1.5
  • phosphonates fosetyl (J.1 .6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), potassium or sodium bicarbonate (J.1 .9);
  • bronopol K.1.1
  • chinomethionat K.1 .2
  • cyflufenamid K.1 .3
  • cymoxanil K.1.4
  • dazomet K.1.5
  • debacarb K.1.6
  • diclomezine K.1 .7
  • difenzoquat K.1 .8
  • difenzoquat-methylsulfate K.1.9
  • diphenylamin K.1 .10
  • fenpyrazamine K.1 .1 1
  • flumetover K.1 .12
  • flusulfamide K.1.13
  • flutianil K.1.14)
  • methasulfocarb K.1 .15
  • nitrapyrin K.1 .16
  • nitrothal-isopropyl K.1.18
  • oxathiapiprolin K.1 .19
  • tolprocarb K.1 .20
  • fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are com- briefly available.
  • fungicides described by lUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583;
  • a compound II selected from the group of the azoles is preferred, especially prochloraz, prothiocona- zole, tebuconazole and triticonazole, especially prothioconazole and triticonazole.
  • Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A or Table A", with triticonazole as compound II are particularly preferred.
  • Mixtures of compounds of formula I as individualized herein, e.g. in Table A, Table A' or Table A", with prothioconazole as compound II are particularly preferred.
  • a compound II selected from the group of benomyl, carbendazim, epoxiconazole, fluquin- conazole, flutriafol, flusilazole, metconazole, prochloraz, prothioconazole, tebuconazole, triticonazole, pyraclostrobin, trifloxystrobin, boscalid, dimethomorph, penthiopyrad, dodemorph, famoxadone, fenpropimorph, proquinazid, pyrimethanil, tridemorph, compound ll-TFPTAP (5- chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine), maneb, mancozeb, metiram, thiram, chloro
  • a compound of formula (I) in mixture with pyraclostrobin is applied, preferably in the methods for seed treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the plant propagation material of the cultivated plant, preferably seeds, wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with pyraclostrobin is applied, preferably in the methods for foliar treat- ment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the cultivated plant, parts of the cultivated plant or to their habitat wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with fluxapyroxad is applied, preferably in the methods for foliar treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the cultivated plant, parts of the cultivated plant or to their habitat wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • a compound of formula (I) in mixture with an azole is applied, preferably in the methods for foliar treatment, i.e. methods, wherein the compound of formula (I) or a mixture thereof is applied to the cultivated plant, parts of the cultivated plant or to their habitat wherein the compound of formula (I) is preferably selected from the compounds 1-1 to I-82 as defined in Table A, more specifically compound 1-1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 as defined in Table A'.
  • the mixtures comprise as an additional component which is the compound against which the cultivated plant is resistant.
  • the ratios by weight for the respective mixtures comprising the insecticidal compound I and compound II are from 1 :500 to 500:1 , preferably from 1 :100 to 100:1 , more preferably from 1 :25 to 25:1.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
  • An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof.
  • the term "pesticidally effective amount" is defined below.
  • the compounds of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, pow- ders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi-ers and binders.
  • suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants,
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo ⁇ hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alkyl
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox- ylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth- oxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or al- kylpolyglucosides.
  • polymeric surfactants are homo- or copolymers of vinylpyrroli- done, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or pol- yethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxi- laries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, pol- yacrylates, biological or synthetic waxes, and cellulose ethers.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the in- vention or partially premixed components e. g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
  • the compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infes- tation by animal pests, with a pesticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions compris- ing said mixtures as defined above.
  • the components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application.
  • Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
  • Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
  • furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the pesticidally active compound to plant foli- age, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as
  • the term "contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
  • animal pest includes arthropods, gastropods, and nematodes.
  • Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
  • Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
  • crop refers to both, growing and harvested crops.
  • plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • iceberg lettuce chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cu- curbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g.
  • Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
  • Plants which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice.
  • rapeseed e.g. oilseed rape
  • bean carnation
  • chicory cotton
  • eggplant eucalyptus
  • flax flax
  • lentil eucalyptus
  • melon melon
  • papaya petunia
  • plum poplar
  • potato rice
  • soybean zucchini
  • sugar beet sugarcane
  • sunflower sweet pepper
  • sweet pepper tobacco, tomato
  • the one or more mutagenized or integrated genes are preferably selected from pat, epsps, crylAb, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5.
  • the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant.
  • Such properties include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control.
  • herbicide tolerance e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance
  • mutagenesis for example Clearfield® oilseed rape being tolerant to imidazoli- nones, e.g. imazamox.
  • genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • glyphosate and glufosinate some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • herbicides such as glyphosate and glufosinate
  • RoundupReady® glyphosate
  • LibertyLink® glufosinate
  • insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance.
  • Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance.
  • the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
  • plant propagation material refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the present invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects.
  • the present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermina- tion with a compound of the present invention.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
  • seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the present invention also comprises seeds coated with or containing the active compound.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
  • Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, ba- nanas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include for example flowable concentrates FS, solu- tions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.
  • the active substance concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1 -800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
  • a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein.
  • the amount of the compound of the present invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • the compounds of the present invention may also be used for improving the health of a plant. Therefore, the present invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the present invention.
  • an effective and non-phytotoxic amount means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
  • plant and “plant propagation material” are defined above.
  • Plant health is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).
  • yield for example increased biomass and/or increased content of valuable ingredients
  • quality for example improved content or composition of certain ingredients or shelf life
  • plant vigour for example improved plant growth and/or greener leaves ("greening effect")
  • tolerance to abiotic for example drought
  • biotic stress for example disease
  • production efficiency for example, harvesting efficiency, processability
  • the above identified indicators for the health condition of a plant may be interdependent and may result from each other.
  • Each indicator is defined in the art and can be determined by methods known to a skilled person.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of a cultivated plant, in particular the yield of a cultivated plant, by treating plant propagation material, preferably seeds with compounds of formula I and their mixtures.
  • the present invention also comprises plant propagation material, preferably seed, of a cultivated plant treated with compounds of formula I and their mixtures.
  • the present invention relates to a method of controlling harm- ful insects and/or increasing the health of a cultivated plant, in particular the yield of a cultivated plant by treating the cultivated plant, part(s) of such plant or at its locus of growth with compounds of formula I and their mixtures.
  • the term cultivated plant(s) includes "modified plant(s)" and "transgenic plant(s)".
  • the term “cultivated plants” refers to "modified plants”. In one embodiment of the invention, the term “cultivated plants” refers to "transgenic plants”. "Modified plants” are those which have been modified by conventional breeding techniques.
  • the term “modification” means in relation to modified plants a change in the genome, epigenome, tran- scriptome or proteome of the modified plant, as compared to the control, wild type, mother or parent plant whereby the modification confers a trait (or more than one trait) or confers the increase of a trait (or more than one trait) as listed below.
  • the modification may result in the modified plant to be a different, for example a new plant vari- ety than the parental plant.
  • Transgenic plants are those, which genetic material has been modified by the use of recombinant DNA techniques that under natural circumstances can not readily be obtained by cross breeding, mutations or natural recombination, whereby the modification confers a trait (or more than one trait) or confers the increase of a trait (or more than one trait) as listed below as com- pared to the wild-type plant.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant, preferably increase a trait as listed below as compared to the wild-type plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), or to post- transcriptional modifications of oligo- or polypeptides e.g. by glycosylation or polymer additions such as prenylated, acetylated, phosphorylated or farnesylated moieties or PEG moieties.
  • modification when referring to a transgenic plant or parts thereof is understood that the activity, expression level or amount of a gene product or the metabolite content is changed, e.g. increased or decreased, in a specific volume relative to a cor- responding volume of a control, reference or wild-type plant or plant cell, including the de novo creation of the activity or expression.
  • the activity of a polypeptide is increased or generated by expression or overexpresion of the gene coding for said polypeptide which confers a trait or confers the increase of a trait as listed below as compared to the control plant.
  • expression or “gene expression” means the transcription of a specific gene or specific genes or specific genetic construct.
  • expression or “gene expression” in particular means the transcription of a gene or genes or genetic construct into structural RNA (rRNA, tRNA), regulatory RNA (e.g. miRNA, RNAi, RNAa) or mRNA with or without subsequent translation of the latter into a protein.
  • expression in particular means the transcription of a gene or genes or genetic construct into structural RNA (rRNA, tRNA) or mRNA with or without subsequent translation of the latter into a protein. In yet another embodiment it means the transcription of a gene or genes or genetic construct into mRNA.
  • the process includes transcription of DNA and processing of the resulting mRNA product.
  • increased expression or “overexpression” as used herein means any form of expression that is additional to the original wild-type expression level.
  • polypeptide expression of a polypeptide is understood in one embodiment to mean the level of said protein or polypeptide, preferably in an active form, in a cell or organism.
  • the activity of a polypeptide is decreased by decreased expression of the gene coding for said polypeptide which confers a trait or confers the increase of a trait as listed below as compared to the control plant.
  • Reference herein to "decreased expression” or “reduction or substantial elimination” of expression is taken to mean a decrease in endogenous gene expression and/or polypeptide levels and/or polypeptide activity relative to control plants. It comprises further reducing, repressing, decreasing or deleting of an expression product of a nucleic acid molecule.
  • reduction relate to a corresponding change of a property in an organism, a part of an organism such as a tissue, seed, root, tuber, fruit, leave, flower etc. or in a cell.
  • change of a property it is understood that the activity, expression level or amount of a gene product or the metabolite content is changed in a specific volume or in a specific amount of protein relative to a corresponding volume or amount of protein of a control, reference or wild type.
  • the overall activity in the volume is reduced, decreased or deleted in cases if the reduction, decrease or deletion is related to the reduction, decrease or deletion of an activity of a gene product, independent whether the amount of gene product or the specific activity of the gene product or both is reduced, decreased or deleted or whether the amount, stability or translation efficacy of the nucleic acid sequence or gene encoding for the gene product is reduced, decreased or deleted.
  • reduction include the change of said property in only parts of the subject of the present invention, for example, the modification can be found in compartment of a cell, like an organelle, or in a part of a plant, like tissue, seed, root, leave, tuber, fruit, flower etc. but is not detectable if the overall subject, i.e. complete cell or plant, is tested.
  • the "reduction”, “repression”, “decrease” or “deletion” is found cellular, thus the term “reduction, decrease or deletion of an activity” or “reduction, decrease or deletion of a metabolite content” relates to the cellular reduction, decrease or deletion compared to the wild type cell.
  • the terms “reduction”, “repression”, “decrease” or “deletion” include the change of said property only during different growth phases of the organism used in the inventive process, for example the reduction, repression, decrease or deletion takes place only during the seed growth or during blooming.
  • the terms include a transitional reduction, decrease or deletion for example because the used method, e.g. the antisense, RNAi, snRNA, dsRNA, siRNA, miRNA, ta-siRNA, cosuppression molecule, or ribozyme, is not stable integrated in the genome of the organism or the reduction, decrease, repression or deletion is under control of a regulatory or inducible element, e.g. a chemical or otherwise inducible promoter, and has therefore only a transient effect.
  • a regulatory or inducible element e.g. a chemical or otherwise inducible promoter
  • Reducing, repressing, decreasing or deleting of an expression product of a nucleic acid molecule in modified plants is known.
  • Examples are canola i.e. double nill oilseed rape with reduced amounts of erucic acid and sinapins.
  • Such a decrease can also be achieved for example by the use of recombinant DNA technology, such as antisense or regulatory RNA (e.g. miRNA, RNAi, RNAa) or siRNA approaches.
  • RNAi, snRNA, dsRNA, siRNA, miRNA, ta-siRNA, cosuppression molecule, ribozyme, or antisense nucleic acid molecule a nucleic acid molecule conferring the expression of a domi- nant-negative mutant of a protein or a nucleic acid construct capable to recombine with and silence, inactivate, repress or reduces the activity of an endogenous gene may be used to decrease the activity of a polypeptide in a transgenic plant or parts thereof or a plant cell thereof used in one embodiment of the methods of the invention.
  • transgenic plants with reduced, repressed, decreased or deleted expression product of a nucleic acid molecule are Carica papaya (Papaya plants) with the event name X17-2 of the University of Florida, Prunus domestica (Plum) with the event name C5 of the United States Department of Agriculture - Agricultural Research Service, or those listed in rows T9-48 and T9-49 of table 9 below.
  • plants with increased resistance to nematodes for example by reducing, repressing, de- creasing or deleting of an expression product of a nucleic acid molecule, e.g. from the PCT publication WO 2008/095886.
  • the reduction or substantial elimination is in increasing order of preference at least 10%, 20%, 30%, 40% or 50%, 60%, 70%, 80%, 85%, 90%, or 95%, 96%, 97%, 98%, 99% or more reduced compared to that of control plants.
  • Reference herein to an "endogenous" gene not only refers to the gene in question as found in a plant in its natural form (i.e., without there being any human intervention), but also refers to that same gene (or a substantially homologous nucleic acid/gene) in an isolated form subsequently (re)introduced into a plant (a transgene).
  • control or “reference” are exchangeable and can be a cell or a part of a plant such as an organelle like a chloroplast or a tissue, in particular a plant, which was not modified or treated according to the herein described process according to the invention. Accordingly, the plant used as control or reference corresponds to the plant as much as possible and is as identical to the subject matter of the invention as possible. Thus, the control or reference is treated identically or as identical as possible, saying that only conditions or properties might be different which do not influence the quality of the tested property other than the treatment of the present invention.
  • control or reference plants are wild-type plants.
  • control or reference plants may refer to plants carrying at least one genetic modification, when the plants employed in the process of the present invention carry at least one genetic modification more than said control or reference plants.
  • control or reference plants may be transgenic but differ from transgenic plants employed in the process of the present invention only by said modification contained in the transgenic plants employed in the process of the present invention.
  • wild type or wild-type plants refers to a plant without said genetic modification. These terms can refer to a cell or a part of a plant such as an organelle like a chloroplast or a tissue, in particular a plant, which lacks said genetic modification but is otherwise as identical as possible to the plants with at least one genetic modification employed in the present invention. In a particular embodiment the "wild-type" plant is not transgenic.
  • the wild type is identically treated according to the herein described process according to the invention.
  • the person skilled in the art will recognize if wild-type plants will not require certain treatments in advance to the process of the present invention, e.g. non-transgenic wild- type plants will not need selection for transgenic plants for example by treatment with a select- ing agent such as a herbicide.
  • the control plant may also be a nullizygote of the plant to be assessed.
  • nullizygote refers to a plant that has undergone the same production process as a transgenic, yet has lost the once aquired genetic modification (e.g. due to mendelian segregation)as the corresponding transgenic. If the starting material of said production process is transgenic, then nullizygotes are also transgenic but lack the additional genetic modification introduced by the production process.
  • the purpose of wild-type and nullizygotes is the same as the one for control and reference or parts thereof. All of these serve as controls in any comparison to provide evidence of the advantageous effect of the present invention.
  • any comparison is carried out under analogous conditions.
  • analogous conditions means that all conditions such as, for example, culture or growing conditions, soil, nutrient, water content of the soil, temperature, humidity or surrounding air or soil, assay conditions (such as buffer composition, temperature, substrates, pathogen strain, concentrations and the like) are kept identical between the experiments to be compared.
  • assay conditions such as buffer composition, temperature, substrates, pathogen strain, concentrations and the like.
  • results can be normalized or standardized based on the control.
  • the "reference”, “control”, or “wild type” is preferably a plant, which was not modified or treated according to the herein described process of the invention and is in any other property as similar to a plant, employed in the process of the present invention of the invention as possible.
  • the reference, control or wild type is in its genome, transcriptome, proteome or metabolome as similar as possible to a plant, employed in the process of the present invention of the present inven- tion.
  • the term “reference-” "control-” or “wild-type-” plant relates to a plant, which is nearly genetically identical to the organelle, cell, tissue or organism, in particular plant, of the present invention or a part thereof preferably 90% or more, e.g.
  • the "reference”, “control”, or “wild type” is a plant, which is genetically identical to the plant, cell, a tissue or organelle used according to the process of the invention except that the responsible or activity conferring nucleic acid molecules or the gene product encoded by them have been amended, manipulated, exchanged or introduced in the organelle, cell, tissue, plant, employed in the process of the present invention.
  • the reference and the subject matter of the invention are compared after standardi- zation and normalization, e.g. to the amount of total RNA, DNA, or protein or activity or expression of reference genes, like housekeeping genes, such as ubiquitin, actin or ribosomal proteins.
  • the genetic modification carried in the organelle, cell, tissue, in particular plant used in the process of the present invention is in one embodiment stable e.g. due to a stable transgenic inte- gration or to a stable mutation in the corresponding endogenous gene or to a modulation of the expression or of the behaviour of a gene, or transient, e.g. due to an transient transformation or temporary addition of a modulator such as an agonist or antagonist or inducible, e.g. after transformation with a inducible construct carrying a nucleic acid molecule under control of a inducible promoter and adding the inducer, e.g. tetracycline.
  • a modulator such as an agonist or antagonist or inducible
  • preferred plants from which "modified plants” and/or “transgenic plants” are be selected from the group consisting of cereals, such as maize (corn), wheat, barley sorghum, rice, rye, millet, triticale, oat, pseudocereals (such as buckwheat and quinoa), alfalfa, apples, banana, beet, broccoli, Brussels sprouts, cabbage, canola (rapeseed), carrot, cauliflower, cherries, chickpea, Chinese cabbage, Chinese mustard, collard, cotton, cranberries, creeping bent- grass, cucumber, eggplant, flax, grape, grapefruit, kale, kiwi, kohlrabi, melon, mizuna, mustard, papaya, peanut, pears, pepper, persimmons, pigeonpea, pineapple, plum, potato, raspberry, rutabaga, soybean, squash, strawberries, sugar beet, sugarcane, sunflower, sweet corn, tobacco, tomato, turnip, walnut, water
  • alfalfa canola (rapeseed), cotton, rice, maize, cerals (such as wheat, barley, rye, oat), soybean, fruits and vegetables (such as potato, tomato, melon, papaya), pome fruits (such as apple and pear), vine, sugarbeet, sugarcane, rape, citrus fruits (such as citron, lime, orange, pomelo, grapefruit, and mandarin) and stone fruits (such as cherry, apricot and peach), most preferably from cotton, rice, maize, cerals (such as wheat, barley, rye, oat), sorghum, squash, soybean, potato, vine, pome fruits (such as apple), citrus fruits (such as citron and orange), sugarbeet, sugarcane, rape, oilseed rape and tomatoes,, utmost preferably from cotton, rice, maize, wheat, barley, rye, oat, soybean, potato, vine
  • the cultivated plant is a gymnosperm plant, especially a spruce, pine or fir.
  • the invention relates to methods and uses, wherein a compound of fomula IA as defined herein, is applied in an application type which corresponds in each case to one row of Table AP-T.
  • the invention relates to methods and uses, wherein a compound selected from the compounds of Table A, A' or A", is applied in an application type which corresponds in each case to one row of Table AP-T.
  • the invention relates to methods and uses, wherein a compound of formula 1-1 1 , is applied in an application type which corresponds in each case to one row of Table AP-T.
  • the invention relates to methods and uses, wherein a compound of formula 1-16, is applied in an application type which corresponds in each case to one row of Table AP-T.
  • the invention relates to methods and uses, wherein a compound of formula 1-21 , is applied in an application type which corresponds in each case to one row of Table AP-T.
  • the invention relates to methods and uses, wherein a compound of for- mula I-26, is applied in an application type which corresponds in each case to one row of Table AP-T.
  • the invention relates to methods and uses, wherein a compound of formula 1-31 , is applied in an application type which corresponds in each case to one row of Table AP-T.
  • the application is on fruiting vegetables, and especially on tomato, on pepper or on eggplant.
  • the application is on leafy vegetables, and especially on cabbage or on lettuce.
  • the application is on tubers (tuber vegetables), and especially on potato or on onion.
  • SPC specialty crops
  • SPC-FV fruiting vegetable
  • SPC-LV leafy vegetable
  • SPC-T tubers
  • ST seed treatment
  • the cultivated plants are plants, which comprise at least one trait.
  • the term "trait” refers to a property, which is present in the plant either by genetic engineering or by conventional breeding techniques. Each trait has to be assessed in relation to its respective control. Examples of traits are:
  • modified nutrient uptake preferably an increased nutrient use efficiency and/or resistance to conditions of nutrient deficiency
  • cultiva plants may also comprise combinations of the aforementioned traits, e.g. they may be tolerant to the action of herbicides and express bacterial toxins.
  • all cultivated plants may also provide combinations of the aforementioned proper- ties, e.g. they may be tolerant to the action of herbicides and express bacterial toxins.
  • Tolerance to herbicides can be obtained by creating insensitivity at the site of action of the herbicide by expression of a target enzyme which is resistant to herbicide; rapid metabolism (conjugation or degradation) of the herbicide by expression of enzymes which inactivate herbicide; or poor uptake and translocation of the herbicide.
  • Examples are the expression of enzymes which are tolerant to the herbicide in comparison to wild type enzymes, such as the expression of 5- enolpyruvylshikimate-3-phosphate synthase (EPSPS), which is tolerant to glyphosate (see e.g. Heck et.al, Crop Sci.
  • EPSPS 5- enolpyruvylshikimate-3-phosphate synthase
  • Gene constructs can be obtained, for example, from micro-organism or plants, which are tolerant to said herbicides, such as the Agrobacterium strain CP4 EPSPS which is resistant to glyphosate; Streptomyces bacteria which are resistance to glufosinate; Arabidopsis, Daucus carota, Pseu- domonoas spp. or Zea grass with chimeric gene sequences coding for HDDP (see e.g. WO 1996/38567, WO 2004/55191 ); Arabidopsis thaliana which is resistant to protox inhibitors (see e.g. US 2002/0073443).
  • said herbicides such as the Agrobacterium strain CP4 EPSPS which is resistant to glyphosate; Streptomyces bacteria which are resistance to glufosinate; Arabidopsis, Daucus carota, Pseu- domonoas spp. or Zea grass with chimeric gene sequences
  • Tolerance to glyphosate can also be achieved by any one of the genes 2mepsps, epsps, gat4601 , goxv247 or mepsps.
  • Tolerance to glufosinate can be achieved by any one of the genes bar, pat or pat(syn).
  • the herbicide tolerant plant can be selected from cereals such as wheat, barley, rye, oat; canola, sorghum, soybean, rice, oil seed rape, sugar beet, sugarcane, grapes, lentils, sunflowers, alfalfa, pome fruits; stone fruits; peanuts; coffee; tea; strawberries; turf; vegetables, such as tomatoes, potatoes, cucurbits and lettuce, more preferably, the plant is selected from soybean, maize (corn), rice, cotton, oilseed rape in particular canola, tomatoes, potatoes, sugarcane, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • cereals such as wheat, barley, rye, oat
  • canola, sorghum soybean
  • rice oil seed rape
  • sugar beet sugarcane
  • grapes lentils
  • sunflowers alfalfa
  • pome fruits stone fruits
  • stone fruits peanuts
  • coffee coffee
  • the cultivated plant is selected from the group consisting of Gossypium hirsutum L. (cotton), Zea mays L. (maize), Glycine max L. (soybean), Triticum aestivum (wheat), and Oryza sativa L. (rice), preferably from the group consisting of Gossypium hirsutum L. (cotton), Zea mays L. (maize) and Glycine max L. (soybean).
  • the cultivated plant is Glycine max L. (soybean).
  • Examples of commercial available transgenic plants with tolerance to herbicides are the corn varieties “Roundup Ready Corn”, “Roundup Ready 2" (Monsanto), “Agrisure GT”, “Agrisure GT/CB/LL”, “Agrisure GT/RW”, practiceAgrisure 3000GT” (Syngenta), “YieldGard VT Rootworm/RR2" and “YieldGard VT Triple” (Monsanto) with tolerance to glyphosate; the corn varieties “Liberty Link” (Bayer), “Herculex I”, “Herculex RW”, “Herculex Xtra”(Dow, Pioneer), “Agrisure GT/CB/LL” and “Agrisure CB/LL/RW” (Syngenta) with tolerance to glufosinate; the soybean varieties “Roundup Ready Soybean” (Monsanto) and “Optimum GAT” (DuPont, Pioneer) with tolerance to glyphosate; the cotton varieties "Round
  • transgenic plants with herbicide tolerance are commonly known, for instance alfalfa, apple, eucalyptus, flax, grape, lentils, oil seed rape, peas, potato, rice, sugar beet, sunflower, tobacco, tomatom turf grass and wheat with tolerance to glyphosate (see e.g. US 5188642, US 4940835, US 5633435, US 5804425, US 5627061 ); beans, soybean, cotton, peas, potato, sunflower, tomato, tobacco, corn, sorghum and sugarcane with tolerance to dicamba (see e.g.
  • Plants which are capable of synthesising one or more selectively acting bacterial toxins, comprise for example at least one toxin from toxin-producing bacteria, especially those of the genus Bacillus, in particular plants capable of synthesising one or more insecticidal proteins from Bacillus cereus or Bacillus popliae; or insecticidal proteins from Bacillus thuringiensis, such as del- ta.-endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c, or vegetative insecticidal proteins (VIP), e.g.
  • VIP vegetative insecticidal proteins
  • VIP1 , VIP2, VIP3 or VIP3A insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lec- tins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsine inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such
  • a plant is capable of producing a toxin, lectin or inhibitor if it contains at least one cell comprising a nucleic acid sequence encoding said toxin, lectin, inhibitor or inhibitor producing enzyme, and said nucleic acid sequence is transcribed and translated and if ap- intestinalte the resulting protein processed and/or secreted in a constitutive manner or subject to developmental, inducible or tissue-specific regulation.
  • -endotoxins for example CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c, or vegetative in- secticidal proteins (VIP), for example VIP1 , VIP2, VIP3 or VIP3A, expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701 ).
  • a truncated toxin is a truncated CrylA(b), which is expressed in the Bt1 1 maize from Syngen- ta Seed SAS, as described below.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • non- naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of CrylllA055, a cathepsin-D-recognition sequence is inserted into a CrylllA toxin (see WO 2003/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 2003/052073.
  • genes conferring resistance to coleopteran insects include cry34Ab1 , cry35 Ab1 , cry3A, cry3Bb1 , dvsnf7, and mcry3A.
  • genes conferring resistance to lepidopteran insects include cry1A, cry1A.105, crylAb, cry1Ab-Ac, crylAc, cryl C, cryl F, cry1 Fa2, cry2Ab2, cry2Ae, cry9c, mocryl F, pinll, vip3A(a), and vip3Aa20.
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A- 0 367 474, EP-A-0 401 979 and WO 1990/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • the plant capable of expression of bacterial toxins is selected from cereals such as wheat, barley, rye, oat; canola, cotton, eggplant, lettuce, sorghum, soybean, rice, oil seed rape, sugar beet, sugarcane, grapes, lentils, sunflowers, alfalfa, pome fruits; stone fruits; peanuts; coffee; tea; strawberries; turf; vegetables, such as tomatoes, potatoes, cucurbits and lettuce, more preferably, the plant is selected from cotton, soybean, maize (corn), rice, tomatoes, pota- toes, oilseed rape and cereals such as wheat, barley, rye and oat, most preferably from cotton, soybean, maize, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • cereals such as wheat, barley, rye, oat
  • canola cotton, eggplant, lettuce, sorghum, soybean, rice, oil seed rape, sugar beet
  • the cultivated plant is selected from the group consisting of Gossypium hirsutum L. (cotton), Zea mays L. (maize), Glycine max L. (soybean), Triticum aestivum (wheat), and Oryza sativa L. (rice), preferably from the group consisting of Gossypium hirsutum L. (cot- ton), Zea mays L. (maize) and Glycine max L. (soybean).
  • the cultivated plant is Glycine max L. (soybean).
  • Examples of commercial available transgenic plants capable of expression of bacterial toxins are the corn varieties “YieldGard corn rootworm” (Monsanto), “YieldGard VT” (Monsanto), “Her- culex RW” (Dow, Pioneer), “Herculex Rootworm” (Dow, Pioneer) and “Agrisure CRW” (Syngen- ta) with resistance against corn rootworm; the corn varieties “YieldGard corn borer” (Monsanto), precedeYieldGard VT Pro” (Monsanto), “Agrisure CB/LL” (Syngenta), “Agrisure 3000GT” (Syngenta), "Hercules I", “Hercules II” (Dow, Pioneer), “KnockOut” (Novartis), preferNatureGard” (Mycogen) and consequentStarl_ink” (Aventis) with resistance against corn borer, the corn varieties favorHerculex I" (Dow, Pioneer) and concurrentHerculex
  • transgenic plants with insect resistance are commonly known, such as yellow stemborer resistant rice (see e.g. Molecular Breeding, Volume 18, 2006, Number 1 ), lep- idopteran resistant lettuce (see e.g. US 5349124 ), resistant soybean (see e.g. US 7432421 ) and rice with resistance against Lepidopterans, such as rice stemborer, rice skipper, rice cutworm, rice caseworm, rice leaffolder and rice armyworm (see e.g. WO 2001021821 ).
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • plants which are capable of synthesising antipathogenic substances are selected from soybean, maize (corn), rice, tomatoes, potato, banana, papaya, tobacco, grape, plum and cereals such as wheat, barley, rye and oat, most preferably from soybean, maize (corn), rice, cotton, tomatoes, potato, banana, papaya, oil seed rape, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • Plants which are capable of synthesising antipathogenic substances having a selective action are for example plants expressing the so-called "pathogenesis-related proteins” (PRPs, see e.g. EP-A-0 392 225) or so-called “antifungal proteins” (AFPs, see e.g. US 6864068).
  • PRPs pathogenesis-related proteins
  • AFPs antifungal proteins
  • a wide range of antifungal proteins with activity against plant pathogenic fungi have been isolated from certain plant species and are common knowledge. Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 93/05153, WO 95/33818, and EP-A-0 353 191.
  • Transgenic plants which are resistant against fungal, viral and bacterial pathogens are produced by intro- ducing plant resistance genes.
  • Numerous resistant genes have been identified, isolated and were used to improve plant resistant, such as the N gene which was introduced into tobacco lines that are susceptible to Tobacco Mosaic Virus (TMV) in order to produce TMV-resistant tobacco plants (see e.g. US 5571706), the Prf gene, which was introduced into plants to obtain enhanced pathogen resistance (see e.g. WO 199802545) and the Rps2 gene from Arabidopsis thaliana, which was used to create resistance to bacterial pathogens including Pseudomonas syringae (see e.g. WO 199528423).
  • TMV Tobacco Mosaic Virus
  • Plants exhibiting systemic acquired resistance response were obtained by introducing a nucleic acid molecule encoding the TIR domain of the N gene (see e.g. US 6630618).
  • Further examples of known resistance genes are the Xa21 gene, which has been introduced into a number of rice cultivars (see e.g. US 5952485, US 5977434, WO 1999/09151 , WO 1996/22375), the Rcg1 gene for colletotrichum resistance (see e.g. US 2006/225152), the prpl gene (see e.g. US 5859332, WO 2008/017706), the ppv-cp gene to introduce resistance against plum pox virus (see e.g.
  • the P1 gene for potato virus Y resistance see e.g. US 5968828
  • the HA5-1 gene see e.g. US5877403 and US6046384
  • the PIP gene to indroduce a broad resistant to viruses such as potato virus X (PVX), potato virus Y (PVY), potato leafroll virus (PLRV) (see e.g. EP 0707069) and genes such as Arabidopsis NI 16, ScaM4 and ScaM5 genes to obtain fungal resistance (see e.g. US 6706952 and EP 1018553).
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glu- canases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 1995/33818) or protein or polypeptide factors involved in plant pathogen defense (so-called "plant disease resistance genes", as described in WO
  • Antipathogenic substances produced by the plants are able to protect the plants against a variety of pathogens, such as fungi, viruses and bacteria.
  • Useful plants of elevated interest in connection with present invention are cereals, such as wheat, barley, rye and oat; soybean; maize; rice; alfalfa, cotton, sugar beet, sugarcane, tobacco , potato, banana, oil seed rape; pome fruits; stone fruits; peanuts; coffee; tea; strawberries; turf; vines and vegetables, such as tomatoes, potatoes, cucurbits, papaya, melon, lenses and lettuce, more preferably selected from soybean, maize (corn), alfalfa, cotton, potato, banana, papaya, rice, tomatoes and cereals such as wheat, barley, rye and oat, most preferably from soybean, maize (corn), rice, cotton, potato, tomato, oilseed rape, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • Transgenic plants with resistance against fungal pathogens are, for examples, soybeans with resistance against Asian soybean rust (see e.g. WO 2008/017706); plants such as alfalfa, corn, cotton, sugar beet, oileed, rape, tomato, soybean, wheat, potato and tobacco with resistance against Phytophtora infestans (see e.g.
  • WO 1999064600 plants such as rice, wheat, barley, rye, corn, oats, potato, melon, soybean and sorghum with resistance against fusarium diseases, such as Fusarium graminearum, Fusarium sporotrichioides, Fusarium lateritium, Fusarium pseudograminearum Fusarium sam- bucinum, Fusarium culmorum, Fusarium poae, Fusarium acuminatum, Fusarium equiseti (see e.g.
  • plants such as corn, soybean, cereals (in particular wheat, rye, barley, oats, rye, rice), tobacco, sorghum, sugarcane and potatoes with broad fungal resistance (see e.g. US 5689046, US 6706952, EP 1018553 and US 6020129).
  • Transgenic plants with resistance against bacterial pathogens are, for examples, rice with resistance against Xylella fastidiosa (see e.g. US 6232528); plants, such as rice, cotton, soybean, potato, sorghum, corn, wheat, balrey, sugarcane, tomato and pepper, with resistance against bacterial blight (see e.g. WO 2006/42145, US 5952485, US 5977434, WO 1999/09151 , WO 1996/22375); tomato with resistance against Pseudomonas syringae (see e.g. Can. J. Plant Path., 1983, 5: 251 -255).
  • Transgenic plants with resistance against viral pathogens are, for examples, stone fruits, such as plum, almond, apricot, cherry, peach, nectarine, with resistance against plum pox virus (PPV, see e.g. US PP15,154Ps, EP 0626449); potatoes with resistance against potato virus Y (see e.g. US 5968828); plants such as potato, tomato, cucumber and leguminosaes which are re- sistant against tomato spotted wilt virus (TSWV, see e.g. EP 0626449, US 5973135); corn with resistance against maize streak virus (see e.g. US 6040496); papaya with resistance against papaya ring spot virus (PRSV, see e.g.
  • PRSV papaya with resistance against papaya ring spot virus
  • cucurbitaceae such as cucumber, melon, watermelon and pumpkin, and solanaceae, such as potato, tobacco, tomato, eggplant, paprika and pepper, with resistance against cucumber mosaic virus (CMV, see e.g. US 6849780); cucurbitaceae, such as cucumber, melon, watermelon and pumkin, with resistance against watermelon mosaic virus and zucchini yellow mosaic virus (see e.g. US 6015942); potatoes with resistance against potato leafroll virus (PLRV, see e.g. US 5576202); potatoes with a broad resistance to viruses, such as potato virus X (PVX), potato virus Y (PVY), potato leafroll virus (PLRV) (see e.g. EP 0707069).
  • CMV cucumber mosaic virus
  • PLAV zucchini yellow mosaic virus
  • PVX potato virus X
  • PVY potato virus Y
  • PLRV potato leafroll virus
  • deregulated or commercially available transgenic plants with modified genetic material capable of expression of antipathogenic substances are the following plants: Carica papaya (papaya), Event: 55-1/63-1 ; Georgia University, Carica papaya (Papaya); Event: (X17-2); University of Florida, Cucurbita pepo (Squash); Event: (CZW-3); Asgrow (USA); Semi- nis Vegetable Inc. (Canada), Cucurbita pepo (Squash); Event: (ZW20); Upjohn (USA); Seminis Vegetable Inc. (Canada), Prunus domestica (Plum); Event: (C5); United States Department of Agriculture - Agricultural Research Service, Solanum tuberosum L.
  • Transgenic plants with resistance against nematodes are, for examples, soybean plants with resistance to soybean cyst nematodes.
  • U.S. Patent Nos. 5,589,622 and 5,824,876 are directed to the identification of plant genes expressed specifically in or adjacent to the feeding site of the plant after attachment by the nematode.
  • transgenic plants with reduced feeding structures for parasitic nematodes e.g. plants resistant to herbicides except of those parts or those cells that are nematode feeding sites and treating such plant with a herbicide to prevent, reduce or limit nematode feeding by damaging or destroying feeding sites (e.g. US 5866777).
  • RNAi to target essential nematode genes has been proposed, for example, in PCT Publication WO 2001/96584, WO 2001/17654, US 2004/0098761 , US 2005/0091713, US
  • Transgenic nematode resistant plants have been disclosed, for example in the PCT publications WO 2008/095886 and WO 2008/095889.
  • Plants wich are resistant to antibiotics, such as kanamycin, neomycin and ampicillin.
  • the naturally occurring bacterial nptll gene expresses the enzyme that blocks the effects of the antibiot- ics kanamycin and neomycin.
  • the ampicillin resistance gene ampR also known as blaTEMI
  • ampR is derived from the bacterium Salmonella paratyphi and is used as a marker gene in the transformation of micro-organisms and plants. It is responsible for the synthesis of the enzyme beta- lactamase, which neutralises antibiotics in the penicillin group, including ampicillin.
  • Transgenic plants with resistance against antibiotics are, for examples potato, tomato, flax, canola, oilseed rape and corn (see e.g.
  • Plant Cell Reports 20, 2001 , 610-615. Trends in Plant Science, 1 1 , 2006, 317-319. Plant Molecular Biology, 37, 1998, 287-296. Mol Gen Genet., 257, 1998, 606- 13.). Plant Cell Reports, 6, 1987, 333-336. Federal Register (USA), Vol.60, No.1 13, 1995, page 31 139. Federal Register (USA), Vol.67, No.226, 2002, page 70392. Federal Register (USA), Vol.63, No.88, 1998, page 25194. Federal Register (USA), Vol.60, No.141 , 1995, page 37870. Canadian Food Inspection Agency, FD/OFB-095-264-A, October 1999, FD/OFB-099-127-A, October 1999.
  • the plant is selected from soybean, maize (corn), rice, cotton, oilseed rape, potato, sugarcane, alfalfa, tomatoes and cereals, such as wheat, barley, rye and oat, most preferably from soybean, maize (corn), rice, cotton, oilseed rape, tomato, potato, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • Plants which are tolerant to stress conditions are plants, which show increased tolerance to abiotic stress conditions such as drought, high salinity, high light intensities, high UV irradiation, chemical pollution (such as high heavy metal concentration), low or high temperatures, limitied supply of nutrients (i.e. nitrogen, phosphorous) and population stress.
  • abiotic stress conditions such as drought, high salinity, high light intensities, high UV irradiation, chemical pollution (such as high heavy metal concentration), low or high temperatures, limitied supply of nutrients (i.e. nitrogen, phosphorous) and population stress.
  • transgenic plants with resistance to stress conditions are selected from rice, corn, soybean, sugarcane, alfalfa, wheat, tomato, potato, barley, rapeseed, beans, oats, sorghum and cotton with tolerance to drought (see e.g.
  • the plant is selected from soybean, maize (corn), rice, cotton, sugarcane, alfalfa, sugar beet, potato, oilseed rape, tomatoes and cereals such as wheat, barley, rye and oat, most preferably from soybean, maize (corn), rice, cotton, oilseed rape, tomato, potato, sugarcane, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • Altered maturation properties are for example delayed ripening, delayed softening and early maturity.
  • transgenic plants with modified maturation properties are, selected from tomato, melon, raspberry, strawberry, muskmelon, pepper and papaya with delayed ripening (see e.g. US 5767376, US 7084321 , US 6107548, US 5981831 , WO 1995035387, US
  • the plant is selected from fruits, such as tomato, vine, melon, papaya, banana, pepper, raspberry and strawberry; stone fruits, such as cherry, apricot and peach; pome fruits, such as apple and pear; and citrus fruits, such as citron, lime, orange, pomelo, grapefruit, and mandarin T more preferably from tomato, vine, apple, banana, orange and straw- berry, most preferably tomatoes.
  • fruits such as tomato, vine, melon, papaya, banana, pepper, raspberry and strawberry
  • stone fruits such as cherry, apricot and peach
  • pome fruits such as apple and pear
  • citrus fruits such as citron, lime, orange, pomelo, grapefruit, and mandarin T more preferably from tomato, vine, apple, banana, orange and straw- berry, most preferably tomatoes.
  • Content modification is synthesis of modified chemical compounds (if compared to the corresponding control plant) or synthesis of enhanced amounts of chemical (if compounds compared to the corresponding control plant) and corresponds to an increased or reduced amount of vitamins, amino acids, proteins and starch, different oils and a reduced amount of nicotine.
  • Further transgenic plants with altered content are, for example, potato and corn with modified amylopectin content (see e.g. US 6784338, US 20070261 136); canola, corn, cotton, grape, catalpa, cattail, rice, soybean, wheat, sunflower, balsam pear and vernonia with a modified oil content (see e.g.
  • the plant is selected from soybean, maize (corn), rice, cotton, sugarcane, potato, tomato, oilseed rape, flax and cereals such as wheat, barley, rye and oat, most preferably soybean, maize (corn), rice, oilseed rape, potato, tomato, cotton, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • soybean, maize (corn) rice, cotton, sugarcane, potato, tomato, oilseed rape, flax and cereals
  • wheat, barley, rye and oat most preferably soybean, maize (corn), rice, oilseed rape, potato, tomato, cotton, vine, apple, pear, citron, orange and cereals such as wheat, barley, rye and oat.
  • transgenic plants with enhanced nitrogen assimilatory and utilization capacities are selected from for example, canola, corn, wheat, sunflower, rice, tobacco, soybean, cotton, alfalfa, tomato, wheat, potato, sugar beet, sugar cane and rapeseed (see e.g. WO 1995/00991 1 , WO 1997/030163, US 6084153, US 5955651 and US 6864405).
  • Plants with improved phosphorous uptake are, for example, tomato and potato (see e.g. US 7417181 ).
  • the plant is selected from soybean, maize (corn), rice, cotton, sugarcane, alfalfa, potato, oilseed rape and cereals such as wheat, barley, rye and oat, most preferably from soybean, maize (corn), rice, cotton, oilseed rape, tomato, potato, vine, apple, pear, citron, orange and cereals such as wheat, barley.
  • Transgenic plants with male steriliy are preferably selected from canola, corn, tomato, rice, Indian mustard, wheat, soybean and sunflower (see e.g. US 6720481 , US 6281348, US 5659124, US 6399856, US 7345222, US 7230168, US 6072102, EP1 135982, WO 2001/092544 and WO 1996/040949).
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • the plant is selected from soybean, maize (corn), rice, cotton, oilseed rape, tomato, potato, vine, apple, pear, citron, orange and cereals such as wheat, barley.
  • Plants, which produce higher quality fiber are e.g. transgenic cotton plants.
  • the such improved quality of the fiber is related to improved micronaire of the fiber, increased strength, improved staple length, improved length unifomity and color of the fibers (see e.g. WO 1996/26639, US 7329802, US 6472588 and WO 2001/17333).
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • cultivated plants may comprise one or more traits, e.g.
  • Examples of commercial available transgenic plants with two combined properties are the corn varieties “YieldGard Roundup Ready” and YieldGard Roundup Ready 2" (Monsanto) with glyphosate tolerance and resistance to corn borer; the corn variety “Agrisure CB/LL” (Syntenta) with glufosinate tolerance and corn borer resistance; the corn variety “Yield Gard VT Root- worm/RR2” with glyphosate tolerance and corn rootworm resistance; the corn variety “Yield Gard VT Triple” with glyphosate tolerance and resistance against corn rootworm and corn borer; the corn variety "Herculex I” with glufosinate tolerance and lepidopteran resistance (Cry1 F), i.e.
  • Examples of commercial available transgenic plants with three traits are the corn variety "Herculex I / Roundup Ready 2" with glyphosate tolerance, gluphosinate tolerance and lepidopteran resistance (Cry1 F), i.e. against western bean cutworm, corn borer, black cutworm and fall armyworm; the corn variety "YieldGard Plus / Roundup Ready 2" (Monsanto) with glyphosate tolerance, corn rootworm resistance and corn borer resistance; the corn variety “Agrisure GT/CB/LL” (Syngenta) with tolerance to glyphosate tolerance, tolerance to gluphosinate and corn borer resistance; the corn variety "Herculex Xtra” (Dow, Pioneer) with glufosinate tolerance and lepidopteran resistance (Cry1 F + Cry34/35Ab1 ), i.e.
  • the commercial transgenic plant is a soybean variety with glyphosate tolerance and lepidopteran resistance, preferably with one trait of glyphosate tolerance and two traits of lepidopteran resistance.
  • the glyphosate tolerance is through expression of the EPSPS encoding gene from A. tumefaciens strain CP4 (cp4epsps gene), more preferably it is based on the transgenic event MON89788.
  • the lepidopteran resistance is a resistance to lepidopteran pests of soybean, preferably through expresssion of the CrylAC encoding gene from B. thuringiensis, preferably against velvetbean caterpillar (Anticarsia gemmatalis) and soybean looper (Pseudoplusia includens), more preferably it is based on the transgenic event MON87701.
  • the glyphosate tolerance is based on the transgenic event MON89788 and the trait of lepidopteran resistance is achieved through expresssion of the CrylAC encoding gene from B. thuringiensis, preferably against velvetbean caterpillar (Anticarsia gemmatalis) and soybean looper (Pseudoplusia includens), more preferably based on the transgenic event
  • Pseudoplusia includens is a synonym for Chrysodeixis includens.
  • the commercial transgenic plant is "Intacta RR2 PRO" soybean (Monsanto) which claims to offer tolerance to glyphosate herbicide and protection against major soybean pests (velvetbean caterpilar, soybean looper, soybean budborer, bean shoot borer, bollworm, corn stalk borer, Helicoverpa, e.g. Helicoverpa armigera), along with increased yield potential.
  • "Intacta RR2 Pro” is used as a synonym for "IntactaTM Roundup ReadyTM 2 Pro” soybean variety.
  • the invention relates to methods according to the invention wherein the cultivated plant is a soybean variety with glyphosate tolerance and lepidopteran resistance.
  • the invention relates to methods according to the invention, wherein the glyphosate tolerance is through the expression of the cp4epsps gene, or wherein the lepidopteran resistance is through expresssion of the CrylAC encoding gene from B. thuringiensis, or wherein both the glyphosate tolerance is through the expression of the cp4epsps gene and the lepidopteran resistance is through expresssion of the CrylAC encoding gene from B. thuringiensis.
  • the invention relates to methods according to the invention, wherein the glyphosate tolerance is based on the transgenic event MON89788, or wherein the lepidopteran resistance is based on the transgenic event MON87701 , or wherein both the glyphosate tolerance is based on the transgenic event MON89788 and the lepidopteran resistance is based on the transgenic event MON87701 .
  • the invention relates to methods according to the invention, wherein the lepidopteran resistance is against a species selected from the group of velvetbean caterpillar (Anticarsia gemmatalis) and soybean looper (Pseudoplusia includens, Chrysodeixis in- cludens ).
  • the invention relates to methods according to the invention, wherein the cultivated plant is "Intacta RR2 PRO" soybean (Monsanto), which claims to offer tolerance to glyphosate herbicide and protection against major soybean pests (velvetbean caterpilar, soy- bean looper, soybean budborer, bean shoot borer, bollworm, corn stalk borer, Helicoverpa, e.g. Helicoverpa armigera), along with increased yield potential.
  • major soybean pests velvetbean caterpilar, soy- bean looper, soybean budborer, bean shoot borer, bollworm, corn stalk borer, Helicoverpa, e.g. Helicoverpa armigera
  • the invention relates to such methods according to the invention, wherein the pest is selected from the group of stinkbug species (preferably Euschistus heros), Spodoptera frugiperda and Helicoverpa.
  • stinkbug species preferably Euschistus heros
  • Spodoptera frugiperda preferably Spodoptera frugiperda
  • Helicoverpa preferably Helicoverpa.
  • the commercial transgenic plant is a soybean variety selected from “Roundup Ready 2 Yield”, “Intacta RR2 Pro” and “Vistive Gold” (all Monsanto), or “Stearidonic Acid (SDA) Omega-3” (higher content of SDA in soybean, Monsanto).
  • the trait is Bacillus thuringiensis Cry1A.105 and cry2Ab2 and Vector PV-GMIR13196, for Mon87751 soybean (Monsanto).
  • the commercial transgenic plant is a soybean variety with herbicide tolerance and lepidopteran resistance, wherein the control of Lepidopteran pest is based on Bt CrylAc and Cryl F toxins.
  • the insect-resistant and herbicide-tolerant soybean is DAS81419 (see Table A1 , entry A1 -334).
  • the plant has one trait of glyphosate tolerance and two traits of lepidopteran resistance.
  • the glyphosate tolerance is through expression of the EPSPS encoding gene from A. tumefaciens strain CP4, more preferably it is based on the transgenic event MON89788.
  • the lepidopteran resistance is a resistance to lepidopteran pests of soybean, preferably through expresssion of the CrylAC encoding gene from B. thuringiensis, preferably against velvetbean caterpillar (Anticarsia gemmatalis) and soybean looper (Pseudo- plusia includens), more preferably it is based on the transgenic event MON87701.
  • the glyphosate tolerance is based on the transgenic event MON89788 and the trait of lepidopteran resistance is achieved through expresssion of the CrylAC encoding gene from B. thuringiensis, preferably against velvetbean caterpillar (Anticarsia gemmatalis) and soybean looper (Pseudoplusia includens), more preferably based on the transgenic event
  • Pseudoplusia includens is a synonym for Chrysodeixis includens.
  • the commercial transgenic plant is "Intacta RR2 PRO" soybean (Monsanto) which claims to offer tolerance to glyphosate herbicide and protection against major soybean pests (velvetbean caterpilar, soybean looper, soybean budborer, bean shoot borer, bollworm, corn stalk borer, Helicoverpa, e.g. Helicoverpa armigera), along with increased yield potential.
  • the commercial transgenic plant is a corn variety which has above- ground insect protection from “Genuity VT Triple PRO” or “Herculex Xtra” or both of them, and herbicide tolerance from “Roundup Ready 2" and Liberty Link, preferably corn varieties selected from “Genuity SmartStax", “Genuity VT Triple PRO” and “Genuity VT Double PRO” (all Monsanto), optionally as RIB (refuge-in-bag) solution.
  • the commercial transgenic corn plant variety has a drought tolerance trait, preferably "Genuity DroughtGard”.
  • the trait is double-stranded ribonucleic acid (dsRNA), Bacillus thuringiensis Cry3Bb1 protein and vector PV-ZMIR10871 for MON8741 1 corn.
  • the commercial transgenic plant is a cotton variety selected from “Boll- gard II” (insect protection), "Roundup Ready Flex” (herbicide tolerance) and “Bollgard II with Roundup Ready Flex” (both), all Monsanto.
  • the cultivated plants are plants, which comprise at least one trait of insect resistance (preferably by expression of bacterial toxins) and at least one trait selected from
  • the cultivated plants are plants, which are tolerant to the action of herbicides and plants, which express bacterial toxins, which provides resistance against animal pests (such as insects or arachnids or nematodes), wherein the bacterial toxin is preferably a toxin from Bacillus thuriginensis.
  • the plant is preferably selected from cotton, rice, maize, wheat, barley, rye, oat, soybean, potato, vine, apple, pear, citron and orange.
  • the plant is soybean.
  • the invention relates to a method for controlling pests and/or increasing the plant health of a cultivated plant with at least one modification as compared to the respective non-modified control plant, wherein the plant is soybean, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-82 as defined in Table A,. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 as defined in Table A', more specifically compound 1-1 1 , more specifically compound 1-16, more spe- cifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 .
  • the cultivated plants are plants, which are tolerant to the action of herbicides. Further guidance for specific combinations within this utmost preferred embodiment can be found in Table A1 .
  • compounds of formula I and their mixtures may additionally comprise a herbicide III, to which the plant is tolerant.
  • a herbicide III to which the plant is tolerant.
  • compounds of formula I and their mixtures may additionally comprise glyphosate.
  • the cultivated plant is a cultivated plant tolerant to glufonsinate
  • compounds of formula I and their mixtures may additionally comprise glufonisate.
  • the cultivated plant is a cultivated plant tolerant to a imidazolione herbicide
  • compounds of formula I and their mixtures may additionally comprise at least one imidazolione- herbicide.
  • the imidazolionone-herbicide is selected from imazamox, imazethapyr, ima- zapic, imazapyr, imazamethabenz or imazaquin.
  • the cultivated plant is a cultivated plant tolerant to dicamba
  • compounds of formula I and their mixtures may additionally comprise dicamba.
  • the cultivated plant is a cultivated plant tolerant to sethoxidim
  • compounds of formula I and their mixtures may additionally comprise sethoxidim.
  • compounds of formula I and their mixtures may additionally comprise cycloxidim.
  • the present invention also relates to ternary mixtures, comprising a compound of formula I, an insecticide II and a herbicide III.
  • the present invention also relates to ternary mixtures comprising two insecticides and a fungicide.
  • the present invention also relates to ternary mixtures comprising two fungicides and one insecticide.
  • the present invention also relates to ternary mixtures com- prising an insectide, a fungicide and a herbicide.
  • the cultivated plant is selected from the group of plants as mentioned in the paragraphs and tables of this disclosure, preferably as mentioned above.
  • the cultivated plants are plants, which comprise at least one trait selected from herbicide tolerance, insect resistance for example by expression of one or more bacterial toxins, fungal resistance or viral resistance or bacterial resistance by expression of one or more anti- pathogenic substances, stress tolerance, nutrient uptake, nutrient use efficiency, content modification of chemicals present in the cultivated plant compared to the corresponding control plant.
  • the cultivated plants are plants, which comprise at least one trait selected from herbicide tolerance, insect resistance by expression of one or more bacterial toxins, fungal re- sistance or viral resistance or bacterial resistance by expression of one or more antipathogenic substances, stress tolerance, content modification of one or more chemicals present in the cultivated plant compared to the corresponding control plant.
  • the cultivated plants are plants, which are tolerant to the action of herbicides and plants, which express one or more bacterial toxins, which provides resistance against one or more animal pests (such as insects or arachnids or nematodes), wherein the bacterial toxin is preferably a toxin from Bacillus thuriginensis.
  • the cultivated plant is preferably selected from soybean, maize (corn), rice, cotton, sugarcane, alfalfa, potato, oilseed rape, tomatoes and cereals such as wheat, barley, rye and oat, most preferably from soybean, maize (corn), cotton, rice and cereals such as wheat, barley, rye and oat.
  • the cultivated plants are plants, which are given in table 1.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of cultivated plants by treating cultivated plants, parts of such plants, plant propagation materials, or at their locus of growth with compounds of formula I and their mixtures, wherein the plant is a plant, which is rendered tolerant to herbicides, more preferably to herbicides such as glutamine synthetase inhibitors, 5-enol-pyrovyl- shikimate-3-phosphate-synthase inhibitors, acetolactate synthase (ALS) inhibitors, protoporphy- rinogen oxidase (PPO) inhibitors, auxine type herbicides, most preferably to herbicides such as glyphosate, glufosinate, imazapyr, imazapic, imazamox, imazethapyr, imazaquin, imaza- methabenz methyl, dicamba and 2,4-D.
  • herbicides such as glutamine synthetase inhibitors, 5-eno
  • the present invention relates to a method of controlling harmful pests, especially insects, by treating cultivated plants, parts of such plants, plant propagation materials, or at their locus of growth with compounds of formula I and their mixtures compounds of formula I or their mixtures, wherein the plant corresponds to a row of table A1 .
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of cultivated plants by treating plant propagation materials, preferably seeds with compounds of formula I and their mixtures selected from endosulfan, ethiprole and fipronil, wherein the plant corresponds to row of table A1.
  • the invention relates to a method for increasing the health of cultivated plants by treating cultivated plants, parts of such plants, plant propagation materials, or at their locus of growth with the compound of formula I, wherein the plant corresponds to a row of table A1.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of cultivated plants by treating cultivated plants, parts of such plants or their locus of growth with a compound of formula I, which is selected from the compounds 1-1 to I-82 as defined in Table A, wherein the plant has a property or a transgenic event of a plant which corresponds to a row of table A1 , table 1 or table 2.
  • the compound of formula I is more specifically selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 as defined in Table A'.
  • the properties of the mentioned plants are present in addition to the insecticidal trait.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula I, wherein the plant has a property or a transgenic event of a plant which corresponds to a row of table A1 , wherein the compound of formula I is compound 1-1 1 .
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula I , wherein the plant has a property or a transgenic event of a plant which corresponds to a row of table A1 , wherein the compound of formula I is compound 1-16.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula I , wherein the plant has a property or a transgenic event of a plant which corresponds to a row of table A1 wherein the compound of formula I is compound I-26.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula I , wherein the plant has a property or a transgenic event of a plant which corresponds to a row of table A1 wherein the compound of formula I is compound 1-31 .
  • Table A1
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of cultivated plants by treating cultivated plants, parts of such plants, plant propagation materials, or at their locus of growth with the compound of formula I and its mixtures, wherein the plant is a plant, which express at least one insecticidal toxin, preferably a toxin from Bacillus speicies, more preferably from Bacillus thuringiensis.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of cultivated plants by treating plant propagation materials, preferably seeds with the compound of formula I or its mixtures as defined above, prefera- bly wherein the plant corresponds to a row of table A2 or table 3.
  • the compound of formula I is compound 1-1 1 .
  • the compound of formula I is compound 1-16.
  • the compound of formula I is compound 1-21.
  • the compound of formula I is compound I-26. .
  • the compound of formula I is compound 1-31 .
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of cultivated plants by treating cultivated plants, parts of such plants or at their locus of growth with the compound of formula I and its mixtures wherein the plant corresponds to a row of table A2 or table 3. .
  • the compound of formula I is compound 1-1 1.
  • the compound of formula I is compound 1-16.
  • the compound of formula I is compound 1-21.
  • the compound of formula I is compound I-26.
  • the compound of formula I is compound 1-31 .
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or at their locus of growth with the compound of formula I and its mixtures, wherein the plant corresponds to a row of table A2 or table 3.
  • the compound of formula I is compound 1-1 1.
  • the compound of formula I is compound 1-16.
  • the compound of formula I is compound 1-21.
  • the compound of formula I is compound I-26. .
  • the compound of formula I is compound 1-31 .
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating plant propagation materials, preferably seeds of cultivated plants of cultivated crops with the compound of formula I and its mixtures, wherein the plant corresponds to a row of table A2 or table 3.
  • the com- pound of formula I is compound 1-1 1.
  • the compound of formula I is compound 1-16.
  • the compound of formula I is compound 1-21.
  • the compound of formula I is compound I-26. .
  • the compound of formula I is compound 1-31 .
  • Table A2
  • A2-4 Lepidoptera COT102 (SYN- Gossypium hirsu- available, Syngenta Seeds, resistance IR102-7) tum L. (cotton) Inc.
  • a * refers to contestZhuxian B", WO2001021821 , Molecular Breeding, Volume 18, Number 1 / August 2006.
  • the cultivated plant has an arthropodicidal, preferably insecticidal, trait, it often occurs that the pest that should be combatted becomes resistant to that trait.
  • Resistance may be defined as 'a heritable change in the sensitivity of a pest population that is reflected in the repeated failure of a product to achieve the expected level of control when used according to the label recommendation for that pest species'.
  • IRAC Iron Resistance therefore means that the original activitiy of a pesticide against the target organisms (arthropods, insects) decreases or is even lost, due to genetic or metabolic adaptation of the target organism.
  • Resistant to an insecticide is understood to mean resistant to at least one insecticide or insecticidal trait, i.e. the insect may be resistant to only one, but also to several insecticides or insecticidal traits.
  • the resistance is against an insecticidal effect which is due to a genetic modification of a plant (modified or transgenic plant), which caused a resistance of the plant or crop to certain pests, especially insect pests, in susceptible insects.
  • insecticidal proteins especially those mentioned herein, es- pecially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., and so on.
  • VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
  • insecticidal proteins of bacteria colonizing nematodes for example Photorhabdus spp. or Xenorhabdus spp., and so on.
  • the present invention relates to a method of controlling harmful insects by treating cultivated plants, parts of such plants or their locus of growth with a compound of formula (I) or a mixture thereof, wherein the plant has at least one insecti- cidal trait, and wherein the harmful insects are resistant to that at least one insecticidal trait of the plant.
  • the present invention relates to a method of controlling harmful insects by treating cultivated plants, parts of such plants or their locus of growth with a compound of formula (I) or a mixture thereof, wherein the plant has at least one lepidopteran or coleopteran trait, and wherein the harmful insects are resistant to that lepidopteran or coleopteran insecticidal trait of the plant.
  • a compound of formula (I) or a mixture thereof wherein the plant has at least one lepidopteran or coleopteran trait, and wherein the harmful insects are resistant to that lepidopteran or coleopteran insecticidal trait of the plant.
  • the present invention relates to a method of controlling harmful insects by treating cultivated plants, parts of such plants or their locus of growth with a compound of formula (I) or a mixture thereof, wherein the plant having the insecticidal trait corresponds to a row of table A2 or Table 3 or Table A1 , and wherein the harmful insects are resistant to an insecticidal trait of the plant.
  • the invention relates to such methods according to the invention, wherein the pest is selected from the group of stinkbug species (preferably Euschistus heros), Spodoptera frugiperda and Helicoverpa.
  • stinkbug species preferably Euschistus heros
  • Spodoptera frugiperda preferably Spodoptera frugiperda
  • Helicoverpa preferably Helicoverpa.
  • the compound of formula (I) may optionally be mixed with one or more further pesticides.
  • Methods and uses of the invention as described herein may also involve a step of assessing whether insects are resistant to certain insecticides.
  • This step will in general involve collecting a sample of insects from the area (e.g. crop, field, habitat) to be treated, before actually applying a compound of formula (I), and testing (for example using any suitable phenotypic, biochemical or molecular biological technique applicable) for resistance/sensitivity.
  • the plants may have more traits and/or events, e.g. those described in Table A1 .
  • the cultivated plant is preferably selected from the group consisting of soybean, cotton and maize, wherein the plant has been made tolerant to the action of certain herbicides as described above. It is particularly preferred that the cultivated plant is selected from the group consisting of soybean, cotton and maize, wherein the plant has been made tolerant to the action of glyphosate herbicides.
  • the cultivated plant is a plant, which has been made tolerant to the action of glyphosate herbicides.
  • the plant may have been made tolerant to other herbicides and/or resistant to certain insects, and/or the plant may have been genetically modified otherwise, e.g. in terms of abiotic stress tolerance, altered growth/yield, disease resistance, modified product quality or pollination control system.
  • Third embodiment of the invention is a plant, which has been made tolerant to the action of glyphosate herbicides.
  • the plant may have been made tolerant to other herbicides and/or resistant to certain insects, and/or the plant may have been genetically modified otherwise, e.g. in terms of abiotic stress tolerance, altered growth/yield, disease resistance, modified product quality or pollination control system.
  • the present invention therefore relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula (I) and their mixtures, wherein the plant is a glyphosate herbicide tolerant plant and corresponds to a row of table A1 , table A2 or table 3.
  • the present invention therefore relates to a method of controlling harmful insects and/or increasing the health of plants by treating plant propagation material, preferably seeds with compounds of formula (I) and their mixtures, wherein the plant is a glyphosate herbicide tolerant plant and corresponds to a row of table A1 , table A2 or table 3.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula (I) and their mixtures, wherein the plant is a glyphosate herbicide tolerant plant and corresponds to a row of table A1 , table A2 or table 3.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating plant propagation material, preferably seeds with compounds of formula (I) and their mixtures, wherein the plant is a glyphosate herbicide tolerant plant and corresponds to a row of table A1 , table A2 or table 3.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula (I) and their mixtures, wherein the plant is a glyphosate herbicide tolerant plant and corresponds to a row of table A1 , table A2 or table 3.
  • the present invention relates to a method of controlling harmful insects and/or increasing the health of plants by treating plant propagation material, preferably seeds with compounds of formula (I) and their mixtures wherein the plant is a glyphosate herbicide tolerant plant and corresponds to a row of table A1 , table A2 or table 3.
  • Insect resistance in particular lepidopteran resistance is of growing importance in GMO crops.
  • the cultivated plant is soybean, which has been made resistant to lepidoperan insects.
  • the soybean may have been made tolerant to certain herbicides and/or resistant to other insects, and/or the soybean may have been genetically modified otherwise, e.g. in terms of abiotic stress tolerance, altered growth/yield, disease resistance, modified product quality or pollination control system.
  • the present invention therefore relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with compounds of formula (I) and their mixtures, wherein the plant is a lepidopteran insect resistant soybean and corresponds to a row of table A1 , A2 or table 3.
  • Lepidopteran resistance of soybeans is typically achieved by introducing a gene selected from the group consisting of: crylAc (gene source: Bacillus thuringiensis subsp. Kurstaki strain HD73), cry1 F (gene source: Bacillus thuringiensis var. aizawai), cry1A.105 (gene source: Bacillus thuringiensis subsp.
  • soybeans may be modified e.g. in terms of herbicide tolerance by introducing a suitable gene such as pat (gene source: Strepto- myces viridochromogenes), which provides glufosinate tolerance or cp4 epsps (aroA:CP4) (gene source: Agrobacterium tumefaciens strain CP4), which provides glyphosate tolerance.
  • pat gene source: Strepto- myces viridochromogenes
  • aroA:CP4 gene source: Agrobacterium tumefaciens strain CP4
  • the soybeans are additionally modified in terms of glyphosate tolerance by introduc- ing the gene cp4 epsps (aroA:CP4).
  • the present invention therefore relates to a method of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or their locus of growth with c compounds of formula (I) and their mixtures, wherein the plant is a lepidopteran insect resistant soybean, which has been modified by intro- ducing at least one gene or at least one gene combination, which corresponds to a row of table C.
  • the present invention also relates to a method for controlling pests and/or increasing the plant health of a cultivated plant as compared to the respective non-modified control plant, comprising the application of compounds of formula (I) and their mixtures, to a plant with at least one modification, parts of such plant, plant propagation material, or at its locus of growth, wherein the cultivated plant is Gossypium hirsutum L. (cotton) or Zea mays L. (maize) and comprises at least one gene selected from the group consisting of dvsnf7, cry1A, cry1Ab-Ac, cry1 C, cry2Ab2, cry2Ae, mocryl F; or
  • Glycine max L. (soybean), Triticum aestivum (wheat) or Oryza sativa L. (rice) and comprises at least one gene selected from the group consisting of cry34Ab1 , cry35 Ab1 , cry3A, cry3Bb1 , dvsnf7, mcry3A, cry1A, cry1A.105, crylAb, cry1Ab-Ac, crylAc, cry1 C, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, cry9c, mocryl F, pinll, vip3A(a), vip3Aa20.
  • the present invention also relates to a method for controlling pests and/or increasing the plant health of a cultivated plant as compared to the respective non-modified control plant, comprising the application of compounds of formula (I) and their mixtures, to a plant with at least one modification, parts of such plant, plant propagation material, or at its locus of growth, wherein the cultivated plant is modified by at least one gene according to one row of table D2.
  • the compound of formula I is selected from the compounds 1-1 to I-82 as defined in Table A curat wherein the plant corresponds to a row of table76.
  • the compound of formula I is more specifically selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 as defined in
  • the compound of formula I is compound 1-1 1 .
  • the compound of formula I is compound 1-16.
  • the compound of formula I is compound 1-21 .
  • the compound of formula I is compound I-26.
  • the compound of formula I is compound 1-31 .
  • Further preferred embodiments of the invention are those methods of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or at their locus of growth with compounds of formula I or their mixtures, wherein the plant expresses one or more genes selected from CP4 epsps, pat, bar, CrylAb, CrylAc, Cry3Bb1 , Cry2Ab, Cry1 F, Cry34Ab1 and Cry35Ab1 .
  • the present invention relates to methods of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or at their locus of growth with compounds of formula I or their mixtures, wherein the mixing partner of the compound of formula I is fipronil and the plant expresses one or more genes selected from CP4 epsps, pat, bar, CrylAb, CrylAc, Cry3Bb1 , Cry2Ab, Cry1 F, Cry34Ab1 and Cry35Ab1 .
  • the present invention relates to methods of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or at their locus of growth with compounds of formula I or their mixtures, wherein the mixing partner of the compound of formula I is ethiprole and the plant expresses one or more genes selected from CP4 epsps, pat, bar, CrylAb, CrylAc, Cry3Bb1 , Cry2Ab, Cry1 F, Cry34Ab1 and Cry35Ab1 .
  • the present invention relates to methods of controlling harmful insects and/or increasing the health of plants by treating cultivated plants, parts of such plants or at their locus of growth with compounds of formula I or their mixtures, wherein the mixing partner of the compound of formula lcompound is chlorfenapyr and the plant expresses one or more genes selected from CP4 epsps, pat, bar, CrylAb, CrylAc, Cry3Bb1 , Cry2Ab, Cry1 F, Cry34Ab1 and Cry35Ab1 .
  • the present invention also relates to a method for controlling pests and/or increasing the plant health of a cultivated plant as compared to the respective non-modified control plant, comprising the application of compounds of formula (I) and their mixtures, to a plant with at least one modification, parts of such plant, plant propagation material, or at its locus of growth, wherein the cultivated plant is modified by at least one gene as described in the follow- ing.
  • the compound of formula I is selected from the compounds 1-1 to I-82 as defined in Table A, wherein the plant corresponds to a row of table76.
  • the compound of formula I is more specifically selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 as defined in Table A'.
  • the compound of formula I is compound 1-1 1 .
  • the compound of formula I is compound 1-16.
  • the compound of formula I is compound 1-21 .
  • the compound of formula I is compound I-26.
  • the compound of formula I is compound 1-31 .
  • further embodiments of the invention are those methods of controlling harmful in- sects and/or increasing the health of plants by treating cultivated plants, parts of such plants or at their locus of growth with a compound of formula (I) or a mixture thereof according to the invention, wherein the plant expresses one or more genes selected from aad, ACCase, ALS, AMY797E, APH4, bar, barnase, barstar, bla, bxn, cDHDPS, CP, cmv-cp, CrylAb, CrylAc, Cry1A.105, Cry1 F, Cry1 Fa2, Cry2Ab, Cry34Ab1 , Cry35Ab1 , Cry3A, Cry3Bb1 , Cry9C, dam, DHFR, fad2, fanl , FH, flcrylAb, GAT4601 , GAT4602, gmFAD2-1 , GM-HRA, goxv247, gus,
  • the compounds of formula (I) can be prepared according to standard methods of organic chemistry, or by the processes as described in WO 2007/006670, WO2013/024007, WO2013/024008, WO2013/076092, and the unpublished applications PCT/EP2014/056164, EP13173044.2, PCT/EP2014/060082, and EP14166089.4 d, without being limited to the routes given therein.
  • the characterization can be done by coupled High Performance Liquid Chromatography / mass spectrometry (HPLC/MS), by NMR or by their melting points.
  • HPLC/MS High Performance Liquid Chromatography / mass spectrometry
  • Synergism can be described as an interaction where the combined effect of two or more compounds is greater than the sum of the individual effects of each of the compounds.
  • the presence of a synergistic effect in terms of percent control, between two mixing partners (X and Y) can be calculated using the Colby equation (Colby, S. R., 1967, Calculating Synergistic and Antagonistic Responses in Herbicide Combinations, Weeds, 15, 20-22):
  • the species used is Anticarsia gem- matalis (H ibner) [Thermesia elegantula (Herrich-Schaffer, 1869)], Noctuidae. 5 plants/plot are infested with 3 larvae (stage L2) using a entomological metallic tweezers, totaling 15 larvae per repetition. Larvae used in this trial are e.g. provided by BASF rearing laboratory, Campinas, Brazil.
  • a second infestation is held seven days after application in the same plants and using the same larval numbers.
  • a third infestation might be done if necessary in order to observe residual activi- ty.
  • the mortality (number) and eating damage (%) are evaluated with 01 , 02, 05, 07, 14 and 21 DAA (days after application), comparing to untreated control plants.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

La présente invention se rapporte à des procédés agricoles de lutte contre les organismes nuisibles et/ou d'amélioration de la santé d'une plante cultivée comportant au moins une modification, lesdits procédés faisant appel à des composés d'anthranilamide de formule (I) dans laquelle R1, R2, R3, R4, R5, R6 et k sont tels que définis dans la description, ainsi qu'à des mélanges de ceux-ci. L'invention concerne, en particulier, des procédés de lutte contre les insectes nuisibles infectant des variétés particulières de soja. L'invention concerne, en particulier, des procédés de lutte contre les insectes nuisibles résistants à un caractère insecticide de la plante.
PCT/EP2015/068006 2014-09-02 2015-08-05 Utilisation de composés de n-thio-anthranilamide sur des plantes cultivées Ceased WO2016034352A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017189797A1 (fr) * 2016-04-27 2017-11-02 Valent Biosciences Llc Mélanges synergiques de bacillus thuringiensis ssp. kurstaki et de cyantraniliprole pour la lutte contre la fausse-teigne des crucifères, la légionnaire de la betterave, le térébrant de la canne à sucre et l'arpenteuse du soja

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013024009A1 (fr) * 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2014053395A1 (fr) * 2012-10-01 2014-04-10 Basf Se Utilisation de composés de n-thio-anthranilamide sur des plantes cultivées
WO2014053403A1 (fr) * 2012-10-01 2014-04-10 Basf Se Procédé de lutte contre les insectes résistants aux insecticides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013024009A1 (fr) * 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2014053395A1 (fr) * 2012-10-01 2014-04-10 Basf Se Utilisation de composés de n-thio-anthranilamide sur des plantes cultivées
WO2014053403A1 (fr) * 2012-10-01 2014-04-10 Basf Se Procédé de lutte contre les insectes résistants aux insecticides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017189797A1 (fr) * 2016-04-27 2017-11-02 Valent Biosciences Llc Mélanges synergiques de bacillus thuringiensis ssp. kurstaki et de cyantraniliprole pour la lutte contre la fausse-teigne des crucifères, la légionnaire de la betterave, le térébrant de la canne à sucre et l'arpenteuse du soja
US10278396B2 (en) 2016-04-27 2019-05-07 Valent Biosciences Llc Synergistic Bacillus thuringiensis subsp. kurstaki and cyantraniliprole mixtures for diamondback moth, beet armyworm, sugarcane borer, and soybean looper control

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