Classifications

• • 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 new uses and methods of N-thio-anthranilamide compounds.
• the invention also relates to the use of the compounds of formula (I) itself and their stereoisomers, salts, tautomers or N-oxides, and their mixtures, in non-agronomic applications, especially in nettings, e.g. mosquito nets, and the use against ants, flies, termites and other pests, especially household pests and stored product pests.
• the invention relates to a method for controlling non-crop pests, comprising contacting the pests or their food supply, habitat, breeding grounds or their locus with at least one pesticidally active anthranilamide compound of formula (I):
• R 2 is selected from the group consisting of hydrogen, halogen, halomethyl and cyano;
• R 3 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkinyl, C2-C6-haloalkinyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl,
• R 6 are selected independently of one another from the group consisting of hydrogen, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the aforementioned aliphatic and cycloaliphatic radicals may be substituted with 1 to 10 substituents R e , and phenyl, which is unsubstituted or carries 1 to 5 substituents R f ; or
• R 5 and R 6 together represent a C2-C7-alkylene, C2-C7-alkenylene or
• Ci-C6-alkyl Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, (Ci-C6-alkoxy)carbonyl, Ci-C6-alkylamino and di-(Ci-C6-alkyl)amino, is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Cs- Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein one or more CH2 groups of the aforementioned radical
• k is O or l ;
• n is 0, 1 or 2; or a stereoisomer, salt, tautomer or N-oxide, or a polymorphic crystalline form, a co-crystal or a solvate of a compound or a stereoisomer, salt, tautomer or N-oxide thereof.
• compound of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof is understood to include a polymorphic crystalline form, a co-crystal or a solvate of a compound or a stereoisomer, salt, tautomer or N-oxide.
• the present invention also relates to the use of a compound of formula (I) as defined herein, or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it, for combating non-crop pests.
• the present invention also relates to a method for controlling a population of social insects, which method comprises applying a compound of formula (I) as defined herein, or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it.
• the social insects are preferably termites, ants, wasps and cockroaches.
• the invention also relates to the use of a compound of formula (I) as defined herein, or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it, for controlling a population of social insects
• WO 2007/006670 describes N-thio-anthranilamide compounds with a sulfilimine or sulfoximine group and their use as pesticides.
• PCT/EP2012/065650, PCT/EP2012/065651 , and the unpublished applications US 61/578267, US 61/593897 and US 61/651050 describe certain N- Thio-anthranilamide compounds and their use as pesticides.
• PCT/EP2012/065648, PCT/EP2012/065649 and EP1 1 189973.8 describe processes for the synthesis of N-Thio-anthranilamide compounds.
• 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 stereoisomer, 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 fluo- rine, 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 alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 12 or 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
• Ci-C4-alkyl examples include methyl, ethyl, n-propyl, 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 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropy
• Ci-Cio-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2- methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1 -ethylpentyl, 2-ethylpentyl, 3- ethylpentyl, n-octyl, 1 -methyloctyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propylpentyl, 2-propylpentyl, nonyl, decyl, 2-propylheptyl and 3-propylheptyl.
• alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
• haloalkyl as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloal- kylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms ("Ci-Cio-haloalkyl”), frequently from 1 to 6 carbon atoms (“Ci-C6-haloalkyl”), more frequently 1 to 4 carbon atoms (“Ci-Cio-haloalkyl”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.
• haloalkyl as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.
• haloalkyl moieties are se- lected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halome- thyl, in particular from Ci-C2-fluoroalkyl.
• Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichlorome- thyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloro- fluoromethyl, chlorodifluoromethyl and the like.
• Ci-C2-fluoroalkyl fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like.
• Ci-C2-haloalkyl are, apart those mentioned for Ci- C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 2-chloroethyl, 2,2,-dichloroethyl, 2,2,2- trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1 - bromoethyl, and the like.
• Ci-C4-haloalkyl are, apart those mentioned for C1-C2- haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trif I uoroprop-2-yl , 3-chloropropyl, 4-chlorobutyl and the like.
• cycloalkyi as used herein (and in the cycloalkyi moieties of other groups comprising a cycloalkyi group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicy- die 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.
• bicydic 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.
• cycloalkylene (or cycloalkanediyl) as used herein in each case denotes an cycloalkyi 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.
• halocycloalkyi as used herein (and in the halocycloalkyi moieties of other groups comprising an halocycloalkyi group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicydic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydro- gen atoms are replaced by halogen, in particular by fluorine or chlorine.
• Examples are 1 - and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3- tetrafluorocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2- trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1 -,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1
• cycloalkyl-alkyl used herein denotes a cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkylene group.
• Cs-Cs-cycloalkyl-Ci- C4-alkyl refers to a Cs-Cs-cycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
• Examples are cyclopropylmethyl, cyclo- propylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopen- tylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpro- pyl, and the like.
• alkenyl denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 10 (“C2-Cio-alkenyl”), preferably 2 to 6 carbon atoms (“C2-C6-alkenyl”), in particular 2 to 4 carbon atoms (“C2-C4-alkenyl”), and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 - methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 - methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl, 1 -methylethenyl
• 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.
• haloalkenyl as used herein, which may also be expressed as "alkenyl which may be substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 ("C 2 -Cio-haloalkenyl") or 2 to 6 ("C 2 -C 6 -haloalkenyl”) or 2 to 4 (“C 2 -C 4 -haloalkenyl”) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
• alkynyl denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 10 (“C2-Cio-alkynyl”), frequently 2 to 6 (“C2-C6-alkynyl”), preferably 2 to 4 carbon atoms (“C2-C 4 -alkynyl”) and one or two triple bonds in any position, for example C2- C 4 -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentyn
• 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.
• haloalkynyl as used herein, which is also expressed as “alkynyl which may be substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having iusually 3 to 10 carbon atoms (“C2-Cio-haloalkynyl”), frequently 2 to 6 (“C2-C6-haloalkynyl”), preferabyl 2 to 4 carbon atoms (“C2-C 4 -haloalkynyl”), and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
• C2-Cio-haloalkynyl unsaturated straight-chain or branched hydrocarbon radicals having iusually 3 to 10 carbon atoms
• C2-C6-haloalkynyl frequently 2 to 6
• C2-C 4 -haloalkynyl preferabyl 2
• alkoxy denotes in each case a straight-chain or branched alkyl group usually having from 1 to 10 carbon atoms ("Ci-Cio-alkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-alkoxy”), preferably 1 to 4 carbon atoms (“Ci-C 4 -alkoxy”), which is bound to the remain- der of the molecule via an oxygen atom.
• Ci-C2-Alkoxy is methoxy or ethoxy.
• Ci-C 4 -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,
• Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
• C1-C10- Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
• haloalkoxy denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 10 carbon atoms ("Ci-Cio-haloalkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-haloalkoxy”), preferably 1 to 4 carbon atoms (“C1-C4- haloalkoxy”), more preferably 1 to 3 carbon atoms (“Ci-C3-haloalkoxy”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
• Ci-C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHC , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5.
• Ci-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH 2 F)-2-fluoroethoxy, 1 -(CH 2 CI)-2-chloroethoxy, 1 -(CH 2 Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
• Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
• alkoxyalkyl denotes in each case alkyl usually comprising 1 to 6 car- bon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 10, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
• Ci-C6-Alkoxy-Ci-C6-alkyl is a Ci-C6-alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above.
• Examples are CH2OCH3, CH2- OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (l -methylpropoxy)-methyl, (2- methylpropoxy)methyl, CH2-OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2- (l -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1 - methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1 -methylpropoxy)-propyl, 2-(2-
• haloalkoxy-alkyl denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 10, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
• Examples are fluoromethoxymethyl, difluoromethox- ymethyl, trifluoromethoxymethyl, 1 -fluoroethoxymethyl, 2-fluoroethoxymethyl, 1 ,1 - difluoroethoxymethyl, 1 ,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1 ,1 ,2- trifluoroethoxymethyl, 1 ,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethox- ymethyl, 1 -fluoroethoxy-1 -ethyl, 2-fluoroethoxy-1 -ethyl, 1 ,1 -difluoroethoxy-1 -ethyl, 1 ,2- difluoroethoxy-1 -ethyl, 2,2-difluoroethoxy-1 -ethyl, 1 ,1 ,2-trifluoroethoxy-1
• alkylthio (also alkylsulfanyl or alkyl-S-)" as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 10 carbon atoms ("Ci-Cio-alkylthio"), frequently comprising 1 to 6 carbon atoms (“Ci-C6-alkylthio”), preferably 1 to 4 carbon atoms (“Ci-C4-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group.
• Ci-C2-Alkylthio is methylthio or ethylthio.
• Ci-C4-Alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec- butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio).
• C1-C6- Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3- methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1 - ethylpropylthio, hexylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4- methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2- dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,
• Ci-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2- ethylhexylthio and positional isomers thereof.
• Ci-Cio-Alkylthio is additionally, for example, nonyl- thio, decylthio and positional isomers thereof.
• haloalkylthio refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
• Ci-C 2 -Haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHCI 2 , SCCI 3 , chlorofluo- romethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2- chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2- chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichlor
• Ci-C4-Haloalkylthio is additionally, for example,
• Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
• 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-C 2 -alkylsulfinyl refers to a Ci-C 2 -alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
• Ci-C4-alkylsulfinyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
• Ci-C6-alkylsulfinyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
• Ci-C 2 -alkylsulfinyl is methylsulfinyl or 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, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 ,1 -dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl, 1 , 3-d imethyl butylsulfi
• 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
• alkylamino denotes in each case a group -NHR, wherein R is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms (“C1-C6- alkylamino”), preferably 1 to 4 carbon atoms("Ci-C4-alkylamino").
• Ci-C6-alkylamino examples include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso- butylamino, tert-butylamino, and the like.
• dialkylamino denotes in each case a group-NRR', wherein R and R', independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms ("di-(Ci-C6-alkyl)-amino"), preferably 1 to 4 carbon atoms (“di-(Ci-C4- alkyl)-amino").
• Examples of a di-(Ci-C6-alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl- butyl-amino, ethyl-isobutyl-amino, and the like.
• cycloalkylamino denotes in each case a group -NHR, wherein R is a cycloalkyi group usually having from 3 to 8 carbon atoms (“Cs-Cs-cycloalkylamino”), preferably 3 to 6 carbon atoms("C3-C6-cycloalkylamino").
• Cs-Cs-cycloalkylamino are cycloprop- ylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, and the like.
• alkylaminosulfonyl denotes in each case a straight-chain or branched alkylamino group as defined above, which is bound to the remainder of the molecule via a sulfonyl [S(0)2] group.
• alkylaminosulfonyl group examples include methylaminosulfonyl, ethyla- minosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, n-butylaminosulfonyl, 2- butylaminosulfonyl, iso-butylaminosulfonyl, tert-butylaminosulfonyl, and the like.
• dialkylaminosulfonyl denotes in each case a straight-chain or branched alkylamino group as defined above, which is bound to the remainder of the molecule via a sulfonyl [S(0)2] group.
• dialkylaminosulfonyl group examples include dimethylaminosul- fonyl, diethylaminosulfonyl, dipropylaminosulfonyl, dibutylaminosulfonyl, methyl-ethyl- aminosulfonyl, methyl-propyl-aminosulfonyl, methyl-isopropylaminosulfonyl, methyl-butyl- aminosulfonyl, methyl-isobutyl-aminosulfonyl, ethyl-propyl-aminosulfonyl, ethyl- isopropylaminosulfonyl, ethyl-butyl-aminosulfonyl, ethyl-isobutyl-aminosulfonyl, and the like.
• aryl refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.
• heteroaryl refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrimidyl and the like.
• 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, (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, tetrahy- drofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine; or
• 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, sulfur, 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.
• 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.
• Preferred compounds according to the invention are compounds of formulae (I) or a stereoisomer, N-oxide or salt thereof, wherein the salt is an agriculturally or veterinarily acceptable salt.
• the compounds I of formula (I) and their examples include their tautomers, racemic mixtures, individual pure enantiomers and diastereomers and their optically active mixtures.
• Preferred are methods and uses of compounds of formula (I), wherein the compound of formula (I) is a compound of formula IA:
• R 4 is halogen
• R 2 is selected from the group consisting of bromo, chloro, cyano
• R 7 is selected from the group consisting of bromo, chloro, trifluoromethyl. OCHF2, and wherein the variables R 2 , R 7 , R 5 , R 6 and k are as defined herein.
• R 1 is selected from the group consisting of halogen and halomethyl
• R 2 is selected from the group consisting of bromo, chloro and cyano
• R 1 is selected from the group consisting of halogen, methyl and halomethyl
• R 2 is selected from the group consisting of bromo, chloro and cyano
• R 5 , R 6 are selected inde- pendently of one another from the group consisting of hydrogen, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, wherein the aforementioned aliphatic and cycloaliphatic radicals may be substituted with 1 to 10 substituents R e ; or
• R 5 , R 6 are selected independently of one another from the group consisting of hydrogen, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, wherein the aforementioned aliphatic and cycloaliphatic radicals may be substituted with 1 to 10 substituents R e .
• R 7 is selected from the group consisting of bromo, difluoromethyl, trifluoromethyl, cyano, OCHF2, OCH2F and
• OCH2CF3 Preferred are methods and uses of compounds of formula (I), in which R 7 is selected from the group consisting of bromo, difluoromethyl, trifluoromethyl and OCH F2.
• R 5 and R 6 are selected from methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, cyclo- propyl, cyclopropylmethyl.
• R 5 and R 6 are identical.
• the methods and uses according to the invention comprise at least one compound of formula (IA)
• R 4 is CI
• R 1 is selected from the group consisting of CI, Br, and methyl
• R 2 is selected from the group consisting of bromo and chloro
• R 5 , R 6 are selected independently of one another from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.
• R 7 is selected from the group consisting of difluoromethyl, trifluoromethyl.
• Examples of especially preferred anthranilamide compounds I of the present invention are of formula (IA-1 )
• R 1 , R 2 , R 7 , R 5 , R 6 are as defined herein.
• Examples of preferred compounds of formula (I) in the methods and uses according to the in- vention are compiled in tables 1 to 60 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
• Table 3 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is CI, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 4 Compounds of the formula (IA-1 ) in which R 1 is methyl, R 2 is CI, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 6 Compounds of the formula (IA-1 ) in which R 1 is Br, R 2 is Br, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 7 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is Br, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 8 Compounds of the formula (IA-1 ) in which R 1 is methyl, R 2 is Br, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 9 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is cyano, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 10 Compounds of the formula (IA-1 ) in which R 1 is Br, R 2 is cyano, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 1 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is cyano, R 7 is CF3 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 14 Compounds of the formula (IA-1 ) in which R 1 is Br, R 2 is CI, R 7 is CHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 15 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is CI, R 7 is CHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 19 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is Br, R 7 is CHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 20 Compounds of the formula (IA-1 ) in which R 1 is methyl, R 2 is Br, R 7 is CHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 28 Compounds of the formula (IA-1 ) in which R 1 is methyl, R 2 is CI, R 7 is Br and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 29 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is Br, R 7 is Br and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 35 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is cyano, R 7 is Br and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 36 Compounds of the formula (IA-1 ) in which R 1 is methyl, R 2 is cyano, R 7 is Br and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 40 Compounds of the formula (IA-1 ) in which R 1 is methyl, R 2 is CI, R 7 is CI and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 41 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is Br, R 7 is CI and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 45 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is cyano, R 7 is CI and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 46 Compounds of the formula (IA-1 ) in which R 1 is Br, R 2 is cyano, R 7 is CI and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 50 Compounds of the formula (IA-1 ) in which R 1 is Br, R 2 is CI, R 7 is OCHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 51 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is CI, R 7 is OCHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 52 Compounds of the formula (IA-1 ) in which R 1 is methyl, R 2 is CI, R 7 is OCHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 53 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is Br, R 7 is OCHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 57 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is cyano, R 7 is OCHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• Table 58 Compounds of the formula (IA-1 ) in which R 1 is Br, R 2 is cyano, R 7 is OCHF 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
• A-52 C2H5 CH CH 2
• A-54 CH2CH2CH 3 CH CH 2 A-96 CH 2 -c-C 3 H 5 CH2CH2CH3
• A-57 C(CH 3 ) 3 CH CH 2 A-99 CH2-C-C6H11 CH2CH2CH3
• A-63 CHF 2 CH CH 2 A-105 CH(CH 3 ) 2 CH(CH 3 ) 2
• A-66 CH2CH2CI CH CH 2 A-108 CH 2 CH(CH 3 ) 2 CH(CH 3 ) 2
• A-67 c-CsHs CH CH 2 A-109 CH(CH 3 )CH 2 CH 3 CH(CH 3 ) 2
• A-69 C-C5H9 CH CH 2 A-1 1 1 CH 2 C ⁇ CH CH(CH 3 ) 2
• A-75 C6H5 CH CH 2 A-1 17 c-CsHs CH(CH 3 ) 2
• A-136 CH 2 C ⁇ CH CH2CH2CH2CH 3 A-178 CH CH 2 CH 2 CH(CH 3 ) 2
• A-160 CH 2 CH CH 2 C(CH 3 ) 3
• A-303 CH CH 2 CHF 2 A-345 c-C 6 Hii CH2CI
• A-328 CH CH 2 CH2CI A-370 c-C 6 Hii CH2CH2CN
• A-460 CH 2 CH CH 2 C-C5H9 A-502 C 2 H5 CH 2 -c-C 3 H 5
• A-628 CH CH 2 CH2-C-C4H7
• A-636 CH 2 C ⁇ CH CH2-C-C4H7
• c-C 3 H 5 cyclopropyl; C-C4H7: cyclobutyl; C-C5H9: cyclopentyl; c-CeHu: cyclohexyl;
• CH2-c-C 3 H 5 cyclopropylmethyl;
• CH(CH 3 )-c-C 3 H 5 1 -cyclopropylethyl;
• CH2-C-C5H9 cyclopentylmethyl
• CH2-C-C5H9 cyclopentylmethyl
• CeH 5 phenyl
• a group of especially preferred compounds of formula (I) are compounds 1-1 to I-40 of formula IA-1 which are listed in the table C in the example section.
• a compound selected from the compounds 1-1 to I-40 as defined in Table C in the Example Section at the end of the description, are preferred in the methods and uses according to the invention.
• a compound selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 is the compound I in the methods and uses according to the invention, which are defined in accord- ance with Table C of the example section: Table C
• 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.
• the compounds of formula (I) as defined herein, or a stereoisomer, salt, tautomer or N-oxide thereof, or the compositions comprising them, are used for combating or controlling non-crop pests.
• the invention also relates to compositions containing compounds of formula (I) in pesticidally effective amounts for controlling non-crop pests.
• the invention further relates to the use of compounds of formula (I) for the protection of nonliving organic materials against non-crop pests.
• non-crop pest control agents such as pyrethroids
• Another problem encountered concerns the need to have available non-crop pest control agents which are effective against a broad spectrum of non-crop pests. Accordingly, there is a need to provide new and improved non-crop pest control agents that overcome these problems. It is therefore an object of the present invention to provide new non-crop pest control agents, preferably exhibiting an enhanced pesticidal spectrum of action.
• Non-crop pests are pests of the classes Chilopoda and Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthop- tera, Siphonap- tera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.
• the compounds of the formula (I) are especially suitable for efficiently combating the following pests:
• centipedes Chilopoda
• Scutigera coleoptrata centipedes
• spiders e.g. Latrodectus mactans, and Loxosceles reclusa
• ⁇ scabies (Acaridida): e.g. sarcoptes sp,
• ticks and parasitic mites ticks (Ixodida), e.g. Ixodes scapularis, Ixodes hol- ocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacen- tor variabilis, Amblyomma americanum, Ambryomma maculatum, Orni- thodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Orni- thonyssus bacoti and Dermanyssus gallinae,
• termites e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalen- sis, and Coptotermes formosanus,
• cockroaches e.g. Blattella germanica, Blattella asahinae, Peri- pla- neta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Peri- planeta australasiae, and Blatta orientalis,
• insects e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivo- rax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Co- chliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefascia
• Earwigs e.g. forficula auricularia, true bugs (Hemiptera), e.g. Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triato- ma spp., Rhodnius prolixus, and Arilus critatus,
• Vespula squamosa Paravespula vulgaris, Pa- ravespula pennsylvanica, Paravespula germanica, Dolicho- vespula maculata, Vespa cra- bro, Polistes rubiginosa, Camponotus floridanus, and Li- nepithema humile,
• crickets grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo- tal- pa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexi- canus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schisto- cerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamo- rus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Cho oicetes terminifera, and Locustana pardaliria, fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenoce
• Crop pest control always is a part of plant protection.
• Non-crop pest control e.g. re- lates to protection of non-living organic materials, or hygiene and disease prevention (public health).
• non-crop pests do not live on plants and do not or only in rare occasions feed on the green parts of the plant.
• Non-crop pests e.g. feed on non-living organic materials such as the homes, clothing and the food etc of human beings and animals but also on electric wires etc thereby introducing pathogenic germs into the human being's environ- ment and destroying their homes and food.
• An example is the termite (order Isoptera) that primarily feeds on cellulose which is the major component of wood and paper products.
• Another example is the mosquito (order Diptera) whose larvae feed on microorganisms and organic matter in the water and whose adults feed on blood.
• the properties of pesticides need to be adapted to their specific use.
• Systemic pesti- cides for example that by virtue of their water-solubility are introduced into the plant parts are suitable for controlling piercing-sucking or biting (i.e. crop) pests.
• they cannot generally be expected to show equal activity against non-crop pests who do not feed on the green plant parts but are controlled by mostly water-insoluble pesticides in baiting systems or by direct treatment.
• crop pest control pesti- cides are not suitable for non-crop pest controlling and vice versa.
• the market insecticides pirimicarb, acephate, pyrimidiven, and pyridaben are examples. They are active against crop insects but show low activity against non-crop pests.
• the invention relates to a method for controlling non-crop pests, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds I- 1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, 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 .
• the non- crop pest is selected from flies, mosquitoes (Diptera).
• the invention relates to a method for controlling non-crop pest which is selected from flies, mosquitoes, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, 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 .
• the non-crop pest is selected from: Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albi- manus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya homi- nivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus,
• the non- crop pest is selected from termites (Isoptera). More preferably, the non-crop pest is selected from: Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalensis, and Cop- totermes formosanus.
• the invention relates to a method for controlling non-crop pest which is se- lected from termites, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, more specifically compound 1-1 1 , more specifically compound I- 16, more specifically compound 1-21 , more specifically compound I-26, more specifically com- pound 1-31 .
• the non- crop pest is selected from ants (Hymenoptera). More preferably, the non-crop pest is selected from: Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomo urn phar- aonis, Solenopsis geminata, Sole- nopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogo- nomyrmex barbatus, Pogo- nomyrmex californicus, Dasymutilla occidentalis, Bombus spp.
• Ves- pula squamosa Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolicho- vespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile.
• the invention relates to a method for controlling non-crop pest which is selected from ants, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, 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 .
• the non- crop pest is selected from crickets, grasshoppers, locusts (Orthoptera). More preferably, the non-crop pest is selected from: Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguini- pes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca ame-ricana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zo- nozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Callip-tamus italicus, Cho oicetes terminifera, and Locustan
• the invention relates to a method for controlling non-crop pest which is selected from crickets, grasshoppers, locusts (Orthoptera), which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, more specifically compound I- 1 1 , more specifically compound 1-16, more specifically compound 1-21 , more specifically compound I-26, more specifically compound 1-31 .
• the invention relates to:
• non-crop pest is selected from flies, mosquitoes (Diptera).
• compounds of formula (I), and their stereoisomers, salts, tautomers and N-oxides, and compositions comprising them are used for the protection of non-living organic materials, including but are not limited to house-hold goods such as fats, oils, mono- oligo- or polyorganosaccharides, proteins, or fresh or decaying fruits; cellulose-containing materials e.g. wooden materials such as houses, trees, board fences, or sleepers and also paper; and also construction materials, furniture, leathers, animal, plant and synthetic fibers, vinyl articles, electric wires and cables as well as styrene foams.
• house-hold goods such as fats, oils, mono- oligo- or polyorganosaccharides, proteins, or fresh or decaying fruits
• cellulose-containing materials e.g. wooden materials such as houses, trees, board fences, or sleepers and also paper
• construction materials furniture, leathers, animal, plant and synthetic fibers, vinyl articles, electric wires and cables as well as styrene foam
• compounds of formula (I), and their stereoisomers, salts, tautomers and N- oxides, and compositions comprising them are used for the protection of non-living organic materials against non-crop pests selected from the group consisting of the class Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Or- thoptera, and Thysanura.
• the invention relates to compounds according to the invention, for the protection of human beings and animals against mosquitos.
• the invention especially relates to textile materials, foils or nettings which comprise or incorporate a compound accord- ing to the invention.
• "incorporated” means embedded.
• "incorporated” means comprised in impregnated form.
• the invention also relates to abovementioned textile material for the protection of plants or crops, e.g. tobacco, nuts, fruits, trees, wood.
• the nettings or textile material can be impregnated in the manner of a composition as described in WO2005/064072 or WO20080/151984.
• the netting material especially a material as described in WO2010/012671 , can be used as a protection in the storage of tobacco as described in WO 2007/144401 , and can also be used in a similar manner for the protection of other goods.
• the use of the compounds according to the invention can be done as described in WO2008/142103. In the protection of living plants, the use of the compounds according to the invention can be done as described in WO2012/038460.
• the foils or nettings can also be used as mulch foil in the protection of crops.
• the invention relates to a netting, which comprises a compound of formula
• the compound I which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accord- ance with Table C of the example section, 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 .
• the invention relates to a method for protecting humans from insects, which method comprises applying a compound of formula I, which is selected from the com- pounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, 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 .
• the invention relates to a method for protecting stored goods, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds I-
• I I , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, 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 .
• the invention relates to a method for protecting stored goods which are selected from tobacco, nuts, cocoa, fruits, wood; which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, 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 .
• the present invention also relates to a method for the protection of non-living organic materials against non-crop pests, preferably against non-crop pests selected from the group consisting of the class Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, He- miptera, Hymenoptera, Orthoptera, and Thysanura, comprising contacting the pests or their food supply, habitat, breeding grounds, their locus or the non-living organic materials them- selves with a pesticidally effective amount of a compound of formula (I), or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it.
• non-crop pests selected from the group consisting of the class Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, He- miptera, Hymenoptera, Orthoptera, and Thysanura
• compounds of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it are preferably used for protecting cellulose-containing non-living organic materials:
• compounds of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it are used for protecting cellulose-containing non-living organic mate- rials against non-crop pests from the Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, and Orthoptera orders, most preferably the Isoptera orders.
• the present invention also provides a method for protecting cellulose-containing nonliving organic materials against non-crop pests, preferably from the Isoptera, Diptera, Blattaria (Blat- todea), Hymenoptera, and Orthoptera orders, most preferably the Isoptera orders, comprising contacting the pests or their food supply, habitat, breeding grounds, their locus or the cellulose- containing non-living organic materials themselves with a pesticidally effective amount of a compound of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it.
• a method for protecting cellulose-containing nonliving organic materials against non-crop pests preferably from the Isoptera, Diptera, Blattaria (Blat- todea), Hymenoptera, and Orthoptera orders, most preferably the Isoptera orders, comprising contacting the pests or their food supply, habitat, breeding grounds, their locus or the cellulose- containing non-living organic materials themselves with
• compounds of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it are used for protecting mono- oligo- or polysaccharides and proteins.
• compounds of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it are used for protecting mono- oligo- or polysaccharides and proteins against non-crop pests selected from the Dermaptera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera, Blattaria (Blattodea), and Hymenoptra orders.
• the present invention also provides a method for protecting mono- oligo- or polysac- charides and proteins against non-crop pests, preferably selected from the Dermaptera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera, Blattaria (Blattodea), and Hymenoptra orders, comprising contacting the pests or their food supply, habitat, breeding grounds or their locus with a pesticidally effective amount of a compounds of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it.
• non-crop pests preferably selected from the Dermaptera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera,
• compounds of formula (I) or a stereoisomer, salt, tautomer or N-oxide thereof, or a composition comprising it are preferably used for protection of animals against non-crop pest of the class Chilopoda, and of the orders Araneida, Hemiptera, Diptera, Phthiraptera, Siphonap- tera, Parasitiformes and Acaridida by treatment of the pests in water bodies and/ or in and around buildings, including but not limited to walls, ground,- manure piles, turf grass, pastures, sewers and materials used in the construction of buildings and also mattresses and bedding, with a pesticidally effective amount of a compound of formula (I) or a composition comprising it.
• compounds of formula (I) are used for protection of animals against non-crop pest of the Diptera, Phthiraptera, Siphonaptera, and Parasitiformes orders.
• Animals include warm-blooded animals, including humans and fish.
• Compounds of formula (I) are preferably used for protection of warm-blooded animals such as cattle, sheep, swine, camels, deer, horses, poultry, rabbits, goats, dogs and cats.
• the invention is also in the technical field of vector control and in particular mosquito and bed bug control.
• the compounds, mixtures and compositions of this invention are used against animal pests such as arthropods which transmit disease pathogens or which annoy the well-being of humans and animals.
• the compounds, mixtures and compositions of this invention are in particular useful to overcome target-specific and/or metabolic-specific resistance of mosquitos and bed bugs.
• the compounds according to the invention are suitable for controlling animal pests and in particular to control insecticide-resistant animal pests. This effect is in particular surprising in connec- tion with the control of insecticide-resistant mosquitos and/or bed bugs.
• the mixtures especially of interest in this context are mixtures of compounds of formula I with ethiprole, fipronil, neonicotionids (i.e. preferably a compound selected from the group of acet- amiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam).
• the compounds, mixtures and compositions of this invention are used to control animal pests, preferably arthropods and more preferably sucking, stinging and chewing insects and arachnids.
• the arachnids include essentially mites (for example Sarcoptes scabiei, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermanyssus gallinae, Acarus siro) and ticks (for example Ixodes ricinus, Ixodes scapularis, Argas reflexus, Ornithodorus moubata, Rhipicepha- lus (Boophilus) microplus, Amblyomma hebraeum, Rhipicephalus sanguineus).
• mites for example Sarcoptes scabiei, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermanyssus gallinae, Acarus siro
• ticks for example Ixodes ricinus, Ixodes scapularis, Argas reflexus, Ornithodorus moubata, Rhipicepha- lus (Boophilus
• the sucking and stinging insects include essentially the mosquitoes (for example Aedes ae- gypti, Aedes albopictus, Aedes vexans, Culex quinquefasciatus, Culex tarsalis, Anopheles al- bimanus, Anopheles stephensi, Anopheles gambiae, Anopheles funestus, Mansonia titillans); the sandflies (for example Phlebotomus papatasii), gnats (for example Culicoides furens), black flies (for example Simulium damnosum); flies such as stinging flies (for example Stomoxys calci- trans), tsetse flies (for example Glossina morsitans morsitans), horse flies (for example Tabanus nigrovittatus, Haematopota pluvialis, Chrysops caecutiens), true
• the chewing insects include essentially cockroaches (for example Blattella germanica, Periplaneta americana, Blatta orientalis, Supella longipalpa); beetles (for example Sitiophilus granarius, Te- nebrio molitor, Dermestes lardarius, Stegobium paniceum, Anobium punctatum, Hylotrupes ba- julus), termites (for example Reticulitermes lucifugus); ants (for example Lasius niger, Mon- omorium pharaonis); and larvae of moths (for example Ephestia elutella, Ephestia cautella, Plo- dia interpunctella, Hofmannophila pseudospretella, Tineola bisselliella, Tinea pellionella, Tri- chophaga tapetzella).
• cockroaches for example Blattella germanica, Periplaneta americana, Blatta orientalis, Supella long
• the compounds, mixtures and compositions of the present invention are used to control insects and arachnids selected from the group of mosquitos, ticks, flies, bed bug (Cimex lectularius), ants, beetles, cockroaches and/or termites. Even more preferred, the compounds, mixtures and compositions of the present invention are used to control mosquitos and/or bed bugs.
• a further embodiment of the invention relates to the use of the compounds, mixtures and compositions according to the invention to control insecticide-resistant mosquitos and/or insecticide- resistant bed bugs and more preferably mosquitos and/or bed bugs that are target-site- and/or metabolic-resistant.
• Target-site resistance referes to a form of biochemical resistance which occurs when the insecticide compound no longer binds to its target
• metabolic -resistance refers to a form of biochemical resistance which occurs when levels or modified activities of esterases, oxidases, or glutathione S-transferases (GST) prevent an insecticide compound from reaching its site of action.
• GST glutathione S-transferases
• the compounds, mixtures and compositions of the present invention are preferably used to control insecticide-resistant mosquitos wherein the insecticide- resistant mosquitos are selected from the group of Anopheles gambiae, preferably the strain RSPH and Anopheles funestus, preferably the strain FUMOZ-R.
• the compounds, mixtures and compositions of the present invention are used to control pyrethroid and/or carbamate- resistant mosquitos, preferably pyrethroid and/or carbamate- resistant Anopheles gambiae and/or Anopheles funestus mosquitos.
• the compounds, mixtures and compositions of the present invention are used to control pyrethroid- resistant mosquitos, preferably pyrethroid-resistant Anopheles gambiae and/or Anopheles funes- tus mosquitos.
• Another preferred embodiment of the invention relates to the compounds, mixtures and compositions of the present invention used to control multi-resistant mosquitos.
• the invention also relates to the use of an active compound composition according to the invention to control pyrethroid-resistant bed bugs.
• the active compound composition of the invention is used to control pyrethroid-resistant bed bugs, wherein the bed bugs have a Valine to Leucine mutation (V419L) and/or a Leucine to Isoleucine mutation (L925I) in the voltage-gated sodium channel alpha-subunit gene.
• V419L Valine to Leucine mutation
• L925I Leucine to Isoleucine mutation
• Another embodiment of the invention relates to a method to control animal pests, preferably arthropods, preferably insects and more preferably mosquitos and/or bed bugs in particular insecticide-resistant mosquitos and/or insecticide-resistant bed bugs and more preferably mosqui- tos and/or bed bugs that are target-site- and/or metabolic-resistant.
• Another preferred embodiment relates to a method to control insecticide-resistant mosquitos wherein the insecticide- resistant mosquitos are selected from the group of Anopheles gambiae, preferably the strain RSPH and Anopheles funestus, preferably the strain FUMOZ-R.
• the current invention relates to a method to control pyrethroid and/or carbamate-resistant mosquitos, preferably pyrethroid and/or carbamate-resistant Anopheles gambiae and/ Or Anopheles funestus mosquitos with the active compound composition of the invention. More preferably, the current invention relates to a method to control pyrethroid-resistant mosquitos, preferably pyrethroid-resistant Anopheles gambiae and/or Anopheles funestus mosquitos with the active compound composition of the invention. Another preferred embodiment of the inven- tion relates to a method to control multi-resistant mosquitos with the active compound composition of the invention.
• the invention also relates to a method to control of pyrethroid-resistant bed bugs with the active compound composition of the invention. More preferably, the current invention relates to a method to control pyrethroid-resistant bed bugs that have a Valine to Leucine mutation (V419L) and or a Leucine to Isoleucine mutation (L925I) in the voltage-gated sodium channel alpha- subunit gene.
• V419L Valine to Leucine mutation
• L925I Leucine to Isoleucine mutation
• Another embodiment of the invention relates to a method to overcome insecticide resistance, preferably a target-site and/or metabolic-resistance, in mosquitos and/or bed bugs by applying an active compound composition according to invention to mosquitos and/or bed bugs that have insecticide-resistance respectively a target-site and/or metabolic-resistance.
• the invention relates to a method to overcome insecticide resistance in insecticide- resistant mosquitos selected from the group of Anopheles gambiae, preferably the strain RSPH and Anopheles funestus, preferably the strain FUMOZ-R by applying an active compound composition of the invention to such mosquitos.
• the invention also relates to a method to overcome pyrethroid resistance by applying an active compound composition according to invention to bed bugs that have pyrethroid resistance. More preferably, the compounds, mixtures and compositions of the present invention are used to overcome insecticide resistance in pyrethroid-resistant bed bugs that have a Valine to Leucine mutation (V419L) and/or a Leucine to Isoleucine mutation (L925I) in the voltage-gated sodium channel alpha-subunit gene.
• V419L Valine to Leucine mutation
• L925I Leucine to Isoleucine mutation
• to overcome insecticide-resistance refers to the observation that the compounds, mixtures and compositions of the invention are more efficient in killing a certain insecticide- resistant mosquito than a similarly concentrated active compound from an insecticidial class forwards which such an insecticide- resistant mosquito has developed a resistance.
• Anopheles gambiae the strain RSPH is a multi-resistant mosquito (target-site and metabolic- resistance) that is described in the reagent catalog of the Malaria Research and Reference Reagent Resource Center (www.MR4.org; MR4-number: MRA-334).
• Anopheles funestus, strain FUMOZ-R is a metabolic-resistant strain and is described in Hunt et al., Med Vet Entomol. 2005 Sep; 19(3):271 -5). In this article it has been reported that Anopheles funestus - as one of the major malaria vector mosquitos in Africa - showed resistance to pyrethroids and carbmate insecticides in South Africa.
• Certain Bed bugs are known to be resistant to pyrethroids, wherein the pyrethorids resistance can be ascribed to metabolic resistance such as increased metabolic detoxification by P450s, glutathione transferases, and esterases as well as target-site resistance due to decreased target-site sensitivity of voltage-gated sodium channels. It has been also reported that a Valine to Leucine mutation (V419L) and/or the Leucine to Isoleucine mutation (L925I) in voltage-gated sodium channel alpha-subunit gene is responsible for target-site resistance to deltamethrin in bed bugs (Fan Zhu et al., Archives of Insect Biochemistry and Physiology, 2010, Vol. 00, No 0, 1 -13).
• Pyrethroid and/or carbamate-resistant mosquitos are mosquitos that are resistant to the treatment of pyrethroid insecticides and/or carbamate insecticides.
• Pyrethroid insecticides are e.g. allethrin, bifenthrin, cyfluthrin, cypermethrin, cyphenothrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, imiprothrin, lambda-cyhalothrin, metofluth- rin, permethrin, prallethrin resmethrin, silafluofen, sumithrin, tau-fluvalinate, tefluthrin, tetrame- thrin, tralomethrin, transfluthrin.
• Carbamate insecticides are e.g. aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenobucarb, methiocarb, methomyl, oxamyl, thiodicarb, triazamate.
• Insecticide-resistant mosquitos refers to mosquitos that are resistant to at least one insecticide chemical class.
• Multi-resistant mosquitos refers to a mosquitos where several different resistance mechanisms are present simultaneously such as target-site resistance and metabolic resistance. The different resistance mechanisms may combine to provide resistance to multiple classes of products (IRAC publication: "Preventation and Management of Insecticide Resistance in Vectors of Public Health Importance”; second edition; 201 1 ).
• the compounds, mixtures and compositions according to the invention may comprise further components, for exam- pie additional active compounds of a different type (e.g. other insecticides, antibacterial compounds, fungicides, herbicides etc.) and/or additives customary in crop protection and/or formulation auxiliaries, or may be used together with these compounds.
• the compounds, mixtures and compositions according to the invention have synergistic actions preferably in regard to the above outlined uses.
• the synergistic effects permit a reduction of the application rates, a higher efficacy at the same application rate and/or a reduction in the number of individual applications required and/or to overcome an existing insecticide resistance and - as a result for the user - an economically and ecologically improved control of animal pests and in particular an improved resistant management of mosquitos.
• the invention relates to a method for controlling mosquitoes and/or bed bugs, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C.
• the compound I is selected from compounds 1-1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, more specifically compound 1-1 1 , more specifically compound 1-16, more specifi- cally compound 1-21 , more specifically compound I-26, more specifically compound 1-31 .
• the invention relates to a method for controlling mosquitoes and/or bed bugs, wherein the mosquitoes and/or bed bugs are target-site and/or metabolic-resistant, which method comprises applying a compound of formula I, which is selected from the compounds 1-1 to I-40 as defined in Table C. More specifically, the compound I is selected from compounds I- 1 1 , 1-16, 1-21 , I-26, 1-31 which are defined in accordance with Table C of the example section, 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 .
• the ratio of the compounds of formula I and the mixture partner, and the total amount of the mixture to be employed depend on the species and the occurrence of the arthropods.
• the optimal ratios and overall rates used can be determined for each application by test series.
• mosquitos it may e.g. be from 1 :1 to 1 : 200, preferably from, 1 :1 to 1 : 125, more preferably from 1 :5 to 1 : 125, even more preferably from 1 :25 to 1 :125.
• the application rate of the compounds, mixtures and compositions according to the invention varies preferably within ranges of between 0.001 and 1000 mg/m2, more preferably, 2 and 500 mg/m2 and even more preferred between 5 and 250 mg/m2.
• the compounds, mixtures and compositions of the invention can be converted to the customary compositions as described in this application.
• the compounds, mixtures and compositions of the invention can be used for liquid applications such as e.g a spray solution to control animal pests on a variety of surfaces.
• the treatment of surfaces for example within or ouside from buildings is necessary to control spreading of diseases that are transmitted by arthropods such as insects or arachnids (such as for example mosquitos or bed bugs) that transmit diseases or that annoys animals and humans.
• arthropods such as insects or arachnids (such as for example mosquitos or bed bugs) that transmit diseases or that annoys animals and humans.
• arthropods such as insects or arachnids (such as for example mosquitos or bed bugs) that transmit diseases or that annoys animals and humans.
• arthropods such as insects or arachnids (such as for example mosquitos or bed bugs) that transmit diseases or that annoys animals and humans.
• arthropods such as insects or arachnids (such as for example mosquitos or bed bugs)
• Other uses include the intergration or coating of the active compound composition according to the invention into/of materials such as pellets, granules, dusts, yarns, foils, sleeping mats, mosquito nets, textiles, wovens, braids, knits, felts, nonwovens, curtains, draperies, tarpaulins, fabrics, wood, papers, furnitures, fences in particular animal fences, paints etc. (integration of active ingredients into foils and mosquito nets is e.g. described in WO-A-2009/121580;
• the present invention also relates to a material which comprises the active compound composition of the invention.
• the material is preferably selected from the group of foil, sleeping net, sleeping mat, mosquito net, textile, woven, braid, knit, felt, nonwoven, curtain, drapery, tarpaulin, fabric, wood, paper, furniture, fence preferably animal fence, paint.
• Another preferred em- bodiment of the invention relates to a bed bug bait which comprises the active compound composition of the invention and means to attract bed bugs. Means to attract bed bugs are know to a skilled person in the art (see e.g WO 201 1/149899).
• the compounds, mixtures and composi- tions is used to control bed bugs via an ovicidial activity.
• the compounds, mixtures and compositions of the invention are applied to (e.g. sprayed on) bed bugs and eggs directly (such as e.g. on bedsprings, box springs, and the interior of bed frames or headboards, including all cracks and joints).
• a further embodiment of this invention relates to the use of the above described material to control animal pests, preferably arthropods, preferably insects and more preferably mosquitos and/or bed bugs in particular insecticide-resistant mosquitos and/or insecticide-resistant bed bugs and more preferably mosquitos and/or bed bugs that are target-site- and/or metabolic - resistant.
• Another preferred embodiment relates to the use of such a material to control insecti- cide-resistant mosquitos wherein the insecticide-resistant mosquitos are selected from the group of Anopheles gambiae, preferably the strain RSPH and Anopheles funestus, preferably the strain FUMOZ-R.
• the current invention relates to the use of such a material to control pyrethroid and/or carbamate-resistant mosquitos, preferably pyre- throid and/or carbamate-resistant Anopheles gambiae and/or Anopheles funestus mosquitos.
• the material of the present invention is used to control pyrethroid- resistant mosquitos, preferably pyrethroid-resistant Anopheles gambiae and/or Anopheles funestus mosquitos.
• Another preferred embodiment of the invention relates to the use of such a material to control multi-resistant mosquitos.
• the invention also relates to the use of the above described material to control pyrethroid- resistant bed bugs.
• the material is used to control pyrethroid- resistant bed bugs, wherein the bed bugs have a Valine to Leucine mutation (V419L) and/or a Leucine to Isoleucine mutation (L925I) in the voltage-gated sodium channel alpha-subunit gene.
• the good insecticidal activity of the compounds, mixtures and compositions is illustrated by the examples below. Whereas the individual active compounds show weaknesses in their activity, the combinations show an activity which exceeds a simple addition of activities. In the case of mixtures, a synergistic effect of the active compound combination is always present when the activity of the active compound combination exceeds the total of the activities of the active compounds when applied individually.
• the expected activity for a given combination of two active compounds can be calculated according to S.R. Colby, Weeds 15 (1967), 20-22.
• the short form of the "common name" of an active compound comprises in each case all customary derivatives, such as the esters and salts, and isomers, in particular optical isomers, especially the commercially available form or forms.
• the "common name” refers to an ester or a salt, this in each case also comprises all other customary derivatives, such as other esters and salts, the free acids and neutral compounds, and isomers, in particular optical isomers, especially the commercially available form or forms.
• the subject of the present invention is a method for controlling a population of social insects, especially ants, termites, wasps and cockroaches.
• Social insects are insects which live in a large society, or in a colony comprising a large number of such insects or congeners.
• the control of ants is also desirable as regards the cultivation of fruit trees and/or ornamental trees.
• the reason for this is that certain species of ant provide a role of defending aphids against their predators and thus contribute towards maintaining high populations of aphids, which are harmful to the good health of the trees concerned and/or to fruit yields.
• the pharaoh ant (Monomorium pharaonis) may create anthills even inside living areas, which, in the case of blocks of flats and especially of hospitals, poses hygiene problems.
• the inconvenience and/or damage caused by social insects such as ants or termites or wasps or cockroaches, and preferably ants or cockroaches, are in direct proportion with the sometimes very large number which a population of such insects may reach, for example, in the case of ants, the very large number of individuals in the population of an anthill.
• the known methods moreover have the drawback that it is very difficult to treat all the individuals of the population, especially on account of the fact that, as regards ants, the anthills are fairly inaccessible, since they are generally located at a depth of several tens of centimetres below the surface of the ground.
• One aim of the present invention is to overcome these drawbacks.
• Another aim of the present invention is to ensure the destruction of the larvae present in the anthill, or more generally in the nest or dwelling place of the said social insects.
• Another aim of the present invention is to ensure the destruction of the laying females present in the anthill, or more generally in the nest or dwelling place of the said social insects.
• Another aim of the present invention is to propose a method which allows the definitive destruc- tion of all or almost all of a population of social insects such as ants or termites or wasps or cockroaches, preferably such as ants or cockroaches, or in another embodiment such as termites.
• the subject of the present invention is thus a method for controlling a population of social insects such as ants or termites or wasps or cockroaches, characterized in that there is applied to a minor fraction of this population an effective amount of a composition comprising a bait and a compound of formula (I) as defined herein.
• Populations of ants are more especially preferred among the populations of social insects which may be controlled using the method according to the invention.
• Populations of termites are also more especially preferred among the populations of social insects which may be controlled using the method according to the invention.
• control of a population of social insects such as ants, ter- mites, wasps or cockroaches
• control of the said insects is understood to mean the control of the said insects, and more particularly the total or almost total destruction of the said population, in other words the destruction of more than 60%, preferably more than 70% and even more preferably of 95 to 100%, of the said population.
• An effective amount of the composition used in the method according to the invention is understood to mean an amount which is capable of controlling the whole population of social insects such as a population of ants or termites or wasps or cockroaches.
• the invention relates to a method for treating social insects such as ants, ter- mites, cockroaches or wasps with an effective amount of active material of formula (I), this effective amount of composition being an amount used equal to the dose required to destroy at least 90 percent of the minor fraction of the population of social insects to which the said composition is applied, within a period of between 2 and 30 days, preferably between 2 and 7 days.
• the minor fraction often corresponds in practice to the population living or circulating outside the common dwelling place or nest.
• the effective amount of composition used for the method according to the invention is generally such that the dose of compound of formula (I) is between 0.05 and 50 mg per anthill treated, preferably from 0.1 to 20 mg.
• This effective amount may be determined more precisely within this range by systematic tests, depending on the species of ant whose population it is desired to control, and also depending on the size and extent of the anthills which may vary according to the nature of these species.
• the invention thus also relates to a method for controlling social insects such as ants, termites, wasps or cockroaches (but preferably cockroaches) which have a common dwelling place or nest in which they live with a substantial population of their congeners, the said method comprising a treatment with an effective dose, preferably a dose of between 0.0001 and 20 grams per 100 m 2, of one or more areas frequented by, or assumed to be frequented by, the said social insects (preferably cockroaches), the said area being outside the place of the said common dwelling but being a place in which the cockroaches circulate or are assumed to circulate.
• an effective dose preferably a dose of between 0.0001 and 20 grams per 100 m 2
• the said social insects preferably cockroaches
• the said area being outside the place of the said common dwelling but being a place in which the cockroaches circulate or are assumed to circulate.
• ants which may be controlled using the method according to the invention are especially: ants of the genus Lasius, for example the black ant (Lasius niger);
• fire ants belonging to the genus Solenopsis such as the ants of the genus Acromyrmex (for example the cassaya ant) and the ants of the genus Atta.
• the cockroaches which may be treated by the method of the invention are mainly Blatella ger- manica, Blatella orientalis, Periplaneta americana, Periplaneta fuliginosa.
• the bait employed in the composition used in the method according to the invention is a product which is sufficiently appetizing to incite social insects such as ants or wasps or cockroaches to eat it.
• this bait is chosen, for example, but not exclusively, from animal and/or plant proteins, or alternatively from fats, also of animal and/or plant origin, or even from mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose or even molasses or honey.
• the minor fraction of the population to which the composition employed in the method accord- ing to the invention is applied is generally between 1 and 50 percent of the total population, preferably between 2 and 20 percent.
• the population of ants which may be controlled using the method according to the invention is a population of ants living in the same anthill.
• the minor fraction of the population to which the composition is applied generally consists of workers whose function is to collect food from outside the anthill, these being known as the harvester workers of the anthill.
• the ant or cockroach population which can be controlled by means of the method according to the invention is a population of cockroaches living in the same common dwelling place for cockroaches.
• the dose of compound of formula (I) in the composition used is between 0.0005 and 0.5 percent, preferably between 0.001 and 0.2 percent.
• the percentages corre- sponding to doses are, except where otherwise mentioned, weight/weight percentages.
• the dose of bait in the composition used is generally between 1 and 99 percent, preferably between 30 and 99%.
• the composition used may also comprise other additives such as a solvent for the active material, a flavoring, a preserving agent, a dye or a bitter agent.
• the composition by placing it in a closed bait-carrier box containing openings which are reserved, on account of their size, for the exclusive use of ants or cockroaches, or insects of similar size, in an area where these insects are likely to be found.
• the area may es- pecially be in a public or private place, such as a living area, or alternatively on a balcony, a patio, in a garden or in a field.
• This variant is of improved safety, since it concerns an active material which is liable to present a risk in the case of accidental contact or ingestion by pets or children.
• the details of applications for termites are in principle the same as described herein for ants.
• the methods and uses according to the invention may also be applied in buildings and construction, e.g. houses. According to climatic conditions and occurrence of termites, it may be a relevant goal to protect houses and other buildings from termites.
• the invention relates to:
• non-crop pest is selected from termites (Isoptera).
• non-crop pest is selected from ants (Hyme- noptera).
• non-crop pest is selected from crickets, grasshoppers, locusts (Orthoptera).
• Bait comprising a compound of formula (I) as defined herein.
• a method for controlling a population of social insects comprising contacting the pests or their food supply, habitat, breeding grounds or their locus with at least one pesticidally active anthranilamide compound of formula (I) as defined herein.
• the compounds of formula (I) are used in the form of compositions comprising an auxiliary and at least one compound of formula (I) according to the invention, or a stereoisomer, salt, tautomer or N-oxide thereof.
• a composition comprises a pesticidally effective amount of a compound of formula (I).
• effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling invertebrate pests in non-crop applications, e.g. in the protection of materials and which does not result in a substantial damage to the treated locus or material. Such an amount can vary in a broad range and is dependent on various factors, such as the invertebrate (e.g. insect) species to be controlled, the treated material, the climatic conditions and the specific compound I used.
• compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
• composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
• BR, TB, DT granules
• granules e.g. WG, SG, GR, FG, GG, MG
• insecticidal articles e.g. LN
• gel formulations e.g. GF
• 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, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
• 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, cyclohexanol; 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, alkylated
• 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, sulfates, phosphates, carboxylates, and mixtures thereof.
• sulfonates are alkylarylsulfonates, 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 alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
• Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
• Examples of phosphates are phosphate esters.
• Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
• 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 home- 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 compound I on the target.
• examples are surfactants, mineral or vegetable oils, and other auxilaries. 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 alkylisothiazolinones 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. Examples for composition types and their preparation are:
• a compound I according to the invention 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%.
• the active substance dissolves upon dilution with water.
• a compound I according to the invention 5-25 wt% of a compound I according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
• dispersant e. g. polyvinylpyrrolidone
• organic solvent e.g. cyclohexanone
• a compound I according to the invention 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance.
• dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
• 0,1 -2 wt% thickener e.g. xanthan gum
• 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
• dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
• wt% of a compound I according to the invention are ground in a rotor-stator mill with addi- tion of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
• dispersants e.g. sodium lignosulfonate
• 1 -3 wt% wetting agents e.g. alcohol ethoxylate
• solid carrier e.g. silica gel
• a compound I according to the invention In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. car- boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
• dispersants e.g. sodium lignosulfonate
• 1 -5 wt% thickener e.g. car- boxymethylcellulose
• 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
• organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
• surfactant blend e.g. alkohol ethoxylate and arylphenol ethoxylate
• An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
• methylmethacrylate, methacrylic acid and a di- or triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
• a protective colloid e.g. polyvinyl alcohol
• Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
• an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insolu- ble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylme- thene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
• a polyamine e.g. hexamethylenediamine
• the monomers amount to 1 -10 wt%.
• the wt% relate to the total CS composition.
• Dustable powders (DP, DS)
• 1 -10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
• 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
• solid carrier e.g. silicate
• a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
• organic solvent e.g. aromatic hydrocarbon.
• compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
• auxiliaries such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
• 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 substance.
• the active substanc- es are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
• the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
• oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immedi- ately prior to use.
• 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 compounds of the present invention may be applied with other active ingredients, for example with other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides.
• active ingredients for example with other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides.
• additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix).
• the plant(s) may be sprayed with a
• the compound of formula (I) is combined with one or more other pesticidally active compound(s) II selected from insecticides or fungicides. Therefore, the present invention also relates to methods and uses, wherein a mixture or composition comprising at least one compound of formula (I), or a stereoisomer, tautomer , N-oxide or agriculturally or veterinarily acceptable salt thereof, and at least one further pesticide.
• the compounds of formula (I), and their stereoisomers, salts, tautomers and N-oxides, may be applied with other insecticides as compound II, which are listed in the following categorized list M of pesticides, which are, whenever possible, classified according to the Insecticide Resistance Action Committee (IRAC).
• IRAC Insecticide Resistance Action Committee
• Acetylcholine esterase (AChE) inhibitors from the class of
• a carbamates for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodi- carb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of
• M.1 B organophosphates for example acephate, azamethiphos, azinphos-ethyl, azinphosme- thyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimetho- ate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio- phosphoryl) salicylate, isoxathion, malathion, mecarbam,
• GABA-gated chloride channel antagonists such as:
• M.2A cyclodiene organochlorine compounds as for example endosulfan or chlordane
• M.2B fiproles phenylpyrazoles
• ethiprole phenylpyrazoles
• fipronil flufiprole
• pyrafluprole pyriprole
• M.3A pyrethroids for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifen- thrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta- cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, del- tamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin,
• M.3B sodium channel modulators such as DDT or methoxychlor
• M.4A neonicotinoids for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, niten- pyram, thiacloprid and thiamethoxam; orthe compounds
• M.4A.1 1 -[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8-epoxy-1 H- imidazo[1 ,2-a]azepine; or
• M.4A.2 1 -[(6-chloro-3-pyridyl)methyl]-2-nitro-1 -[(E)-pentylideneamino]guanidine; or
• M.4A.3 1 -[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro-2H- imidazo[1 ,2-a]pyridine; or
• M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;
• M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb, or
• M.8A alkyl halides as methyl bromide and other alkyl halides, or
• M.1 1 Microbial disruptors of insect midgut membranes for example bacillus thunngiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thunngiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thurin- giensis 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.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C pro- pargite, or
• Nicotinic acetylcholine receptor (nAChR) channel blockers for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
• Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;
• Octopamin receptor agonists as for example amitraz
• M.21 A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or
• M.22C 1 [(E)-[2-(4-cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]amino]-3-[4- (difluoromethoxy)phenyl]urea;
• M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or
• Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
• flubendiamide for example flubendiamide, chloranthraniliprole (rynaxypyr®), cyanthraniliprole (cyazypyr®), or the phthalamide compounds
• M.26.4 methyl-2-[3,5-dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5- yl]carbonyl ⁇ amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; or a compound selected from M.26.5a) to M.26.5d):
• M.26.5a N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2-(3-chloro- 2-pyridyl)pyrazole-3-carboxamide;
• M.26.5b 5-chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1 -cyano-1 -methyl- ethyl)carbamoyl]phenyl]pyrazole-3-carboxamide;
• M.26.5c 5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2- pyridyl)pyrazole-3-carboxamide;
• M.26.6 N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)-3-iodo-phthalamide; or M.26.7: 3-chloro-N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)phthalamide;
• M.X insecticidal active compounds of unknown or uncertain mode of action as for example afidopyropen azadirachtin, amidoflumet, benzoximate, bifenazate, bromopropylate, chinomethi- onat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumide or the compound
• M.X.2 cyclopropaneacetic acid, 1 ,1 '-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2- cyclopropylacetyl)oxy]methyl]-1 ,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b- trimethyl-1 1 -oxo-9-(3-pyridinyl)-2H,1 1 H-naphtho[2,1 -b]pyrano[3,4-e]pyran-3,6-diyl] ester, or the compound
• M.X.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.X.6 a compound selected from the group of
• M.X.1 1 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 - oxothietan-3-yl)benzamide; or
• M.Y Biopesticides e.g.
• M.Y-1 Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Bacillus firmus, B. thuringiensis ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, Beauveria bassiana, Burkholderia sp., Chromobacterium sub-tsugae, Cydia pomonella granulo- sis virus, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium (formerly Verticillium lecanii), Metarhizium an-isopliae, M.
• anisopliae var. acridum Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus poppiliae, Pasteuria spp., P. nishizawae, P. reneformis, P. us-agae, Pseudomonas fluorescens, Steinernema feltiae, Streptomces galbus;
• the quinoline derivative flometoquin is shown in WO2006/013896.
• the aminofuranone compounds flupyradifurone is known from WO 2007/1 15644.
• the sulfoximine compound sulfoxaflor is known from WO2007/149134.
• the pyrethroid momfluorothrin is known from US6908945.
• the pyrazole acaricide pyflubumide is known from WO2007/020986.
• the isoxazoline compound M.X.1 has been described in WO2005/085216, M.X.8 in WO2009/002809 and in
• the pyripyropene derivative M.X.2 has been described in WO 2006/129714.
• the spiroketal-substituted cyclic ketoenol derivative M.X.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ke-toenol derivative M.X.4 from WO2008/06791 1.
• Triazoylphenylsulfide like M.X.5 have been described in WO2006/043635 and biological control agents on basis of bacillus firmus in WO2009/124707.
• the neonicotionids M4A.1 is known from WO20120/069266 and WO201 1/06946, the M.4A.2 from WO2013/003977, the M4A.3.from WO2010/069266.
• the metaflumizone analogue M.22C is described in CN 10171577.
• Cyantraniliprole (Cyazypyr) is known from e.g. WO 2004/067528.
• the phthalamides M.26.1 and M.26.2 are both known from WO 2007/101540.
• the anthranilamide M.26.3 has been described in WO 2005/077934.
• the hydrazide compound M.26.4 has been described in WO
• the anthranilamide M.26.5a) is described in WO201 1/085575, the M.26.5b) in WO2008/134969, the M.26.5c) in US201 1/046186 and the M.26.5d in WO2012/034403.
• the diamide compounds M.26.6 and M.26.7 can be found in CN102613183.
• M.X.6a) to M.X.6i) listed in M.X.6 have been described in WO2012/029672.
• the mesoionic antagonist compound M.X.9 was described in WO2012/0921 15, the nemati-cide M.X.10 in WO2013/055584 and the Pyridalyl-type analogue M.X.12 in
• biopesticides from group M.Y, and from group F.XIII as described below, their preparation and their biological activity e.g. against harmful fungi, pests is known (e-Pesticide Manual V 5.2 (ISBN 978 1 901396 85 0) (2008-201 1 ); http://www.epa.gov/opp00001/biopesticides/, see product lists therein; http://www.omri.org/omri-lists, see lists therein; Bio-Pesticides Database BPDB http://sitem.herts.ac.uk/aeru/bpdb/, see A to Z link therein).
• biopesticides are registered and/or are commercially available: aluminium silicate (SCREENTM DUO from Certis LLC, USA), Ampelomyces quisqualis M-10 (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG, Ger- many), Ascophyllum nodosum (Norwegian kelp, Brown kelp) extract (e.g. ORKA GOLD from Becker Underwood, South Africa), Aspergillus flavus NRRL 21882 (e.g. AFLA-GUARD® from Syngenta, CH), Aureobasidium pullulans (e.g.
• B 30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest Inc., USA), B. subtilis GB03 (e.g. KODIAK from Gustafson, Inc., USA), B. subtilis GB07 (EPIC from Gustafson, Inc., USA), B. subtilis QST-713 (NRRL-Nr. B 21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from Agra-Quest Inc., USA), B. subtilis var. amylolique-'faciens FZB24 (e.g. TAEGRO® from Novozyme Biologicals, Inc., USA), B. subtilis var.
• B. subtilis var. amylolique-'faciens FZB24 (e.g. TAEGRO® from Novozyme Biologicals, Inc., USA), B. subtilis var.
• amyloliquefa- ciens D747 e.g. Double Nickel 55 from Certis LLC, USA
• Bacillus thuringiensis ssp. kurstaki SB4 e.g. BETA PRO® from Becker Underwood, South Africa
• Beauveria bassiana GHA BOTANIGARD® 22WGP from Laverlam Int. Corp., USA
• B. bassiana 12256 e.g. BIOEX- PERT® SC from Live Sytems Technology S.A., Colombia
• B. bassiana PRPI 5339 ARSEF number 5339 in the USDA ARS collection of entomopathogenic fungal cultures
• BROADBAND® from Becker Underwood, South Africa
• Bradyrhizobium sp. e.g. VAULT® from Becker Underwood, USA
• B. japonicum e.g. VAULT® from Becker Underwood, USA
• Candida oleophila I-82 e.g. ASPIRE® from Ecogen Inc., USA
• Candida saitoana e.g. BIO- CURE® (in mixture with lysozyme) and BIOCOAT® from Micro Flo Company, USA (BASF SE) and Arysta
• Chitosan e.g. ARMOUR-ZEN from BotriZen Ltd., NZ
• ca- tenulata also named Gliocladium catenulatum (e.g. isolate J 1446: PRESTOP® from Verdera, Finland), Coniothyrium minitans CON/M/91 -08 (e.g. Contans® WG from Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS® from Anchor Bio-Technologies, South Africa), Ecklonia maxima (kelp) extract (e.g. KELPAK SL from Kelp Products Ltd, South Africa), Fusarium oxysporum (e.g.
• Gliocladium catenulatum e.g. isolate J 1446: PRESTOP® from Verdera, Finland
• Coniothyrium minitans CON/M/91 -08 e.g. Contans® WG from Prophyta, Germany
• Cryphonectria parasitica e
• BIO- FOX® from S.I.A.P.A., Italy, FUSACLEAN® from Natural Plant Protection, France
• Glomus intraradices e.g. MYC 4000 from ITHEC, France
• Glomus intraradices RTI-801 e.g. MYKOS from Xtreme Gardening, USA or RTI Reforestation Technologies International; USA
• grapefruit seeds and pulp extract e.g. BC-1000 from Chemie S.A., Chile
• Isaria fumosorosea Apopka-97 ATCC 20874) (PFR-97TM from Certis LLC, USA
• Lecanicillium muscarium (formerly Verticillium lecanii) (e.g.
• MYCOTAL from Koppert BV, Netherlands
• Lecanicillium longisporum KV42 and KV71 e.g. VERTALEC® from Koppert BV, Netherlands
• Metarhizium anisopliae var. acridum IMI 330189 deposited in European Culture Collections CABI) (e.g. GREEN MUSCLE® from Becker Underwood, South Africa)
• M. anisopliae FI-1045 e.g. BIOCANE® from Becker Underwood Pty Ltd, Australia
• M. anisopliae var. acridum FI-985 e.g. GREEN GUARD® SC from Becker Underwood Pty Ltd, Australia
• anisopliae F52 e.g. MET52® Novozymes Biologicals BioAg Group, Canada
• M. anisopliae ICIPE 69 e.g. METATHRhPOL from ICIPE, Kenya
• Metschnikowia fructicola e.g. SHEMER® from Agrogreen, Israel
• Microdochium dimerum e.g. ANTIBOT® from Agrauxine, France
• Neem oil e.g. TRILOGY®, TRIACT® 70 EC from Certis LLC, USA
• Paecilomyces fumosoroseus strain FE 9901 e.g. NO FLYTM from Natural Indus- tries, Inc., USA
• lilacinus DSM 15169 e.g. NEMATA® SC from Live Systems Technology S.A., Colombia
• P. lilacinus BCP2 e.g. PL GOLD from Becker Underwood BioAg SA Ltd, South Africa
• mixture of Paenibacillus alvei NAS6G6 and Bacillus pumilis e.g. BAC-UP from Becker Underwood South Africa
• Penicillium bilaiae e.g. JUMP START® from Novozymes Biologicals BioAg Group, Canada
• Phlebiopsis gigantea e.g. ROTSTOP® from Verdera, Finland
• potassium silicate e.g.
• Sil-MATRIXTM from Certis LLC, USA
• Pseudozyma flocculosa e.g. SPORODEX® from Plant Products Co. Ltd., Canada
• Pythium oligandrum DV74 e.g. POLYVERSUM® from Remeslo SSRO, Biopreparaty, Czech Rep.
• Reynoutria sachlinensis extract e.g. REGALIA® from Marrone Biolnnovations, USA
• Rhizobium leguminosarum bv. phaseolii e.g. RHIZO-STICK from Becker Underwood, USA
• R. I. trifolii e.g. DORMAL from Becker Underwood, USA
• viciae e.g. NODULATOR from Becker Underwood, USA
• Sinorhizobium meliloti e.g. DORMAL ALFALFA from Becker Underwood, USA; NITRAGIN® Gold from Novozymes Biologicals BioAg Group, Canada
• Steinernema feltiae NE- MA->SHIELD® from BioWorks, Inc., USA
• Streptomyces lydicus WYEC 108 e.g. Actinovate® from Natural Industries, Inc., USA, US 5,403,584
• S. violaceusniger YCED-9 e.g.
• T. DT-9® from Natural Industries, Inc., USA, US 5,968,503
• Talaromyces flavus V1 17b e.g. PROTUS® from Prophyta, Germany
• Trichoderma asperellum SKT-1 e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd., Japan
• T. atroviride LC52 e.g. SENTINEL® from Agrimm Technologies Ltd, NZ
• T. fertile JM41 R e.g. RICHPLUSTM from Becker Underwood Bio Ag SA Ltd, South Africa
• T. harzianum T-22 e.g. PLANTSHIELD® der Firma BioWorks Inc., USA
• T. harzianum TH 35 e.g.
• T. harzianum T-39 e.g. TRICHODEX® and TRICHODERMA 2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel
• T. harzianum and T. viride e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ
• T. harzianum ICC012 and T. viride ICC080 e.g. REMEDIER® WP from Isagro Ricerca, Italy
• T. polysporum and T. harzianum e.g. BINAB® from BINAB Bio-Innovation AB, Sweden
• T. stromaticum e.g.
• T. virens GL-21 also named Gliocladium virens
• T. viride e.g. TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F from T. Stanes & Co. Ltd., Indien
• T. viride TV1 e.g. T. viride TV1 from Agribiotec srl, Italy
• Ulocladium oudemansii HRU3 e.g. BOTRY-ZEN® from Botry-Zen Ltd,
• Bacillus amyloliquefaciens AP-136 (NRRL B-50614), B. amyloliquefaciens AP-188 (NRRL B-50615), B. amyloliquefaciens AP-218 (NRRL B-50618), B. amyloliquefaciens AP-219 (NRRL B-50619), B. amyloliquefaciens AP-295 (NRRL B-50620), B. mojavensis AP-209 (No. NRRL B- 50616), B. solisalsi AP-217 (NRRL B-50617), B.
• pumilus strain INR-7 (otherwise referred to as BU-F22 (NRRL B-50153) and BU-F33 (NRRL B-50185)), B. simplex ABU 288 (NRRL B-50340) and B. amyloliquefaciens subsp. plantarum MBI600 (NRRL B-50595) have been mentioned i.a. in US patent appl. 20120149571 , WO 2012/079073.
• Beauveria bassiana DSM 12256 is known from US200020031495.
• Bradyrhizobium japonicum USDA is known from US patent 7,262,151.
• Bacillus amyloliquefaciens subsp. plantarum MBI600 having the accession number NRRL B- 50595 is deposited with the United States Department of Agriculture on Nov. 10, 201 1 under the strain designation Bacillus subtilis 1430. It has also been deposited at The National Collections of Industrial and Marine Bacteria Ltd. (NCIB), Torry Research Station, P.O. Box 31 , 135 Abbey Road, Aberdeen, AB9 8DG, Scotland. under accession number 1237 on December 22, 1986.
• Bacillus amyloliquefaciens MBI600 is known as plant growth-promoting rice seed treatment from Int. J. Microbiol. Res. ISSN 0975-5276, 3(2) (201 1 ), 120-130 and further described e.g.
• Bacillus subtilis MBI600 (or MBI 600 or MBI-600) is identical to Bacillus amyloliquefaciens subsp. plantarum MBI600, formerly Bacillus subtilis MBI600.
• Metarhizium anisopliae IMI33 is commercially available from Becker Underwood as product Green Guard.
• M. anisopliae var acridium strain IMI 330189 (NRRL-50758) is commercially available from Becker Underwood as product Green Muscle.
• Bacillus subtilis strain FB17 was originally isolated from red beet roots in North America (System Appl. Microbiol 27 (2004) 372-379). This Bacillus subtilis strain promotes plant health (US 2010/0260735 A1 ; WO 201 1/109395 A2). B. subtilis FB17 has also been deposited at American Type Culture Collection (ATCC), Manassas, VA, USA, under accession number PTA-1 1857 on April 26, 201 1. Bacillus subtilis strain FB17 may also be referred to as UD1022 or UD10-22.
• the at least one biopesticide II is selected from the groups M.Y-1 to M.Y-2:
• M.Y-1 Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity:
• acridum IMI 330189, Paeci- lomyces fumosoroseus FE 9901 , P. lilacinus DSM 15169, P. lilacinus BCP2, Paeni- bacillus poppiliae Dutky-1940 (NRRL B-2309 ATCC 14706), P. poppiliae KLN 3, P. poppiliae Dutky 1 , Pasteuria spp. Ph3, P. nishizawae PN-1 , P. reneformis Pr-3, P.
• the at least one biopesticide II is selected from group M.Y-1. According to one embodiment of the inventive mixtures, the at least one biopesticide II is selected from M.Y-2.
• the at least one biopesticide II is Bacil- lus amyloliquefaciens subsp. plantarum MBI600. These mixtures are particularly suitable in soybean.
• the at least one biopesticide II is B. pumilus strain INR-7 (otherwise referred to as BU-F22 (NRRL B-50153) and BU-F33 (NRRL B- 50185; see WO 2012/079073). These mixtures are particularly suitable in soybean and corn.
• the at least one biopesticide II is Bacillus pumilus, preferably B. pumilis strain INR-7 (otherwise referred to as BU-F22 (NRRL B- 50153) and BU-F33 (NRRL B-50185). These mixtures are particularly suitable in soybean and corn.
• the at least one biopesticide II is Bacillus simplex, preferably B. simplex strain ABU 288 (NRRL B-50340). These mixtures are particularly suitable in soybean and corn.
• the at least one biopesticide II is selected from Trichoderma asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum; mixture of T. harzia-'num and T. viride; mixture of T. polysporum and T. harzianum; T. stromaticum, T. virens (also named Gliocladium virens) and T. viride; preferably Trichoderma fertile, in particular T. fertile strain JM41 R. These mixtures are particularly suitable in soybean and corn.
• the at least one biopesticide II is Sphaerodes mycoparasitica, preferably Sphaerodes mycoparasitica strain IDAC 301008-01 (also referred to as strain SMCD2220-01 ). These mixtures are particularly suitable in soybean and corn.
• the at least one biopesticide II is Beauveria bassiana, preferably Beauveria bassiana strain PPRI5339. These mixtures are particularly suitable in soybean and corn.
• the at least one biopesticide II is Metarhizium anisopliae or M. anisopliae var. acridium, preferably selectged from M anisolpiae strain IMI33 and M. anisopliae var. acridium strain IMI 330189. These mixtures are particularly suitable in soybean and corn.
• Bradyrhizobium sp. meaning any Bradyrhizobium species and/or strain
• biopesticide II is Bradyrhizobium japonicum (B. japon- icum).
• B. japonicum is not one of the strains TA-1 1 or 532c.
• B. japonicum strains were cultivated using media and fermentation techniques known in the art, e.g. in yeast extract-mannitol broth (YEM) at 27°C for about 5 days.
• USDA refers to United States Department of Agriculture Culture Collection, Beltsville, Md., USA (see e.g. Beltsville Rhizobium Culture Collection Catalog March 1987 ARS-30).
• B. japonicum strain G49 (INRA, Angers, France) is described in Fernandez-Flouret, D. & Cleyet-Marel, J. C. (1987) C R Acad Agric Fr 73, 163-171 ), especially for soybean grown in Europe, in particular in France.
• B. japonicum strain TA-1 1 (TA1 1 NOD+) (NRRL B-18466) is i.a. de- scribed in US 5,021 ,076; AppI Environ Microbiol (1990) 56, 2399-2403 and commercially available as liquid inoculant for soybean (VAULT® NP, Becker Underwood, USA). Further B.
• japonicum strains as example for biopesticide II are described in US2012/0252672A. Further suitable and especially in Canada commercially available strain 532c (The Nitragin Company, Milwaukee, Wisconsin, USA, field isolate from Wisconsin; Nitragin strain collection No. 61A152; Can J Plant Sci 70 (1990), 661 -666).
• strains have been re-classified as a novel species Bradyrhizobium elkanii, e.g. strain USDA 76 (Can. J. Microbiol., 1992, 38, 501 - 505).
• B. japonicum strain is E-109 (variant of strain USDA 138, see e.g. Eur. J. Soil Biol. 45 (2009) 28-35; Biol Fertil Soils (201 1 ) 47:81-89, deposited at Agriculture Collection Laboratory of the Instituto de Microbiologia y Zoologia Agncola (IMYZA), Instituto Nacional de Tecnologi ' a Agropecuaria (INTA), Castelar, Argentina).
• This strain is especially suitable for soybean grown in South America, in particular in Argentina.
• the present invention also relates to mixtures, wherein the at least one biopesticide II is selected from Bradyrhizobium elkanii and Bradyrhizobium liaoningense (B. elkanii and B. liaoningen- se), more preferably from B. elkanii. These mixtures are particularly suitable in soybean. B. elkanii and liaoningense were cultivated using media and fermentation techniques known in the art, e.g. in yeast extract-mannitol broth (YEM) at 27°C for about 5 days.
• YEM yeast extract-mannitol broth
• the present invention also relates to mixtures, wherein the at least one biopesticide II is selected from Bradyrhizobium japonicum (B. japonicum) and further comprisies a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis- jasmone, preferably methyl-jasmonate or cis-jasmone.
• B. japonicum Bradyrhizobium japonicum
• compound III is selected from jasmonic acid or salts or derivatives thereof including cis- jasmone, preferably methyl-jasmonate or cis-jasmone.
• biopesticide II is selected from Bradyrhizobium sp. (Arachis) (B. sp. Arachis) which shall describe the cowpea miscellany cross- inoculation group which includes inter alia indigenous cowpea bradyrhizobia on cowpea (Vigna unguiculata), siratro (Macroptilium atropurpureum), lima bean (Phaseolus lunatus), and peanut (Arachis hypogaea).
• This mixture comprising as biopesticide II B. sp. Arachis is especially suitable for use in peanut, Cowpea, Mung bean, Moth bean, Dune bean, Rice bean, Snake bean and Creeping vigna, in particular peanut.
• the present invention also relates to mixtures wherein the at least one biopesticide II is selected from Bradyrhizobium sp. (Arachis) and further comprises a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis-jasmone, preferably methyl-jasmonate or cis-jasmone.
• the at least one biopesticide II is selected from Bradyrhizobium sp. (Arachis) and further comprises a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis-jasmone, preferably methyl-jasmonate or cis-jasmone.
• the present invention also relates to mixtures, wherein the at least one biopesticide II is selected from Bradyrhizobium sp. (Lupine) (also called B. lupini, B. lupines or Rhizobium lupini). This mixture is especially suitable for use in dry beans and lupins.
• the at least one biopesticide II is selected from Bradyrhizobium sp. (Lupine) (also called B. lupini, B. lupines or Rhizobium lupini).
• This mixture is especially suitable for use in dry beans and lupins.
• B. lupini strain is LL13 (isolated from Lupinus iuteus nodules from French soils; deposited at INRA, Dijon and Angers, France;
• B. lupini strains WU425 isolated in Esperance, Western Australia from a non-Australian legume Ornthopus compressus
• WSM4024 isolated from lupins in Australia by CRS during a 2005 survey
• WSM471 isolated from Ornithopus pinnatus in Oyster Harbour, Western Australia
• the present invention also relates to mixtures wherein the at least one biopesticide II is selected from Bradyrhizobium sp. (Lupine) (B. lupini) and further comprises a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis- jasmone, preferably methyl-jasmonate or cis-jasmone.
• the at least one biopesticide II is selected from Bradyrhizobium sp. (Lupine) (B. lupini) and further comprises a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis- jasmone, preferably methyl-jasmonate or cis-jasmone.
• the present invention also relates to mixtures, wherein the at least one biopesticide II is selected from Mesorhizobium sp. (meaning any Mesorhizobium species and/or strain), more prefera- bly Mesorhizobium ciceri. These mixtures are particularly suitable in cowpea.
• M. loti strains are e.g. M. loti CC829 for Lotus pedunculatus.
• the present invention also relates to mixtures wherein the at least one biopesticide II is selected from Bradyrhizobium sp. (Lupine) (B. lupini) and further comprises a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis- jasmone, preferably methyl-jasmonate or cis-jasmone.
• the at least one biopesticide II is selected from Bradyrhizobium sp. (Lupine) (B. lupini) and further comprises a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis- jasmone, preferably methyl-jasmonate or cis-jasmone.
• the present invention also relates to mixtures wherein the at least one biopesticide II is selected from Mesorhizobium huakuii, also referred to as Rhizobium huakuii (see e.g. Appl. Environ. Microbiol. 201 1 , 77(15), 5513-5516). These mixtures are particularly suitable in Astralagus, e.g. Astalagus sinicus (Chinese milkwetch), Thermopsis, e.g. Thermopsis sinoides (Goldenbanner) and alike.
• Astralagus e.g. Astalagus sinicus (Chinese milkwetch)
• Thermopsis e.g. Thermopsis sinoides (Goldenbanner) and alike.
• M. huakuii strain is HN3015 which was isolated from Astralagus sinicus in a rice-growing field of Southern China (see e.g. World J. Microbiol. Biotechn. (2007) 23(6), 845-851 , ISSN 0959-3993).
• the present invention also relates to mixtures wherein the at least one biopesticide II is selected from Mesorhizobium huakuii and further comprises a compound III, wherein compound III is selected from jasmonic acid or salts or derivatives thereof including cis-jasmone, preferably methyl-jasmonate or cis-jasmone.
• the present invention also relates to mixtures, wherein the at least one biopesticide II is select- ed from Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, more preferably from A. brasilense, in particular selected from A. brasilense strains BR 1 1005 (SP 245) and AZ39 which are both commercially used in Brazil and are obtainable from EM- BRAPA, Brazil. These mixtures are particularly suitable in soybean.
• Humates are humic and fulvic acids extracted from a form of lignite coal and clay, known as leonardite.
• Humic acids are organic acids that occur in humus and other organically derived materials such as peat and certain soft coal. They have been shown to increase fertilizer efficiency in phosphate and micro-nutrient uptake by plants as well as aiding in the development of plant root systems.
• Salts of jasmonic acid (jasmonate) or derivatives include without limitation the jasmonate salts potassium jasmonate, sodium jasmonate, lithium jasmonate, ammonium jasmonate, dime- thylammonium jasmonate, isopropylammonium jasmonate, diolammonium jasmonate, diethtri- ethanolammonium jasmonate, jasmonic acid methyl ester, jasmonic acid amide, jasmonic acid methylamide, jasmonic acid-L-amino acid (amide-linked) conjugates (e.g., conjugates with L- isoleucine, L- valine, L-leucine, or L-phenylalanine), 12-oxo-phytodienoic acid, coronatine, coro- nafacoyl- L-serine, coronafacoyl-L-threonine, methyl esters of 1 - oxo-in
• the microbial pesticides embrace not only the isolated, pure cultures of the respective micro-organism as defined herein, but also its cell-free extract, its suspensions in a whole broth culture or as a metabolite-containing supernatant or a purified metabolite obtained from a whole broth culture of the microorganism or microorganism strain.
• the microbial pesticides embrace not only the isolated, pure cultures of the respective micro-organism as defined herein, but also a cell-free extract thereof or at least one metabolite thereof, and/or a mutant of the respective micro-organism having all the identifying characteristics thereof and also a cell-free extract or at least one metabolite of the mutant.
• Whole broth culture refers to a liquid culture containing both cells and media.
• Supernatant refers to the liquid broth remaining when cells grown in broth are removed by centrifugation, filtration, sedimentation, or other means well known in the art.
• metabolite refers to any compound, substance or byproduct produced by a microorganism (such as fungi and bacteria) that has improves plant growth, water use efficiency of the plant, plant health, plant appearance, or the population of beneficial microorganisms in the soil around the plant activity.
• a microorganism such as fungi and bacteria
• mutant refers a microorganism obtained by direct mutant selection but also includes microorganisms that have been further mutagenized or otherwise manipulated (e.g., via the introduction of a plasmid). Accordingly, embodiments include mutants, variants, and or deriva- tives of the respective microorganism, both naturally occurring and artificially induced mutants. For example, mutants may be induced by subjecting the microorganism to known mutagens, such as N-methyl-nitrosoguanidine, using conventional methods.
• the solid material (dry matter) of the biopesticides (with the exception of oils such as Neem oil, Tagetes oil, etc.) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction medium or the suspension medium in case of liquid formulations of the microbial pesticides).
• the weight ratios and percentages used herein for biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).
• weight ratios and/or percentages refer to the total weight of a prepara- tion of the respective biopesticide with at least 1 x 106 CFU/g ("colony forming units per gram total weight"), preferably with at least 1 x 108 CFU/g, even more preferably from 1 x 108 to 1 x 1012 CFU/g dry matter.
• Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells.
• CFU may also be understood as number of (juvenile) individual nematodes in case of (entomo-'pathogenic) nematode biopesticides, such as Stei- nernema feltiae.
• microbial pesticides may be supplied in any physiological state such as active or dormant.
• dormant active component may be supplied for example frozen, dried, or lyophi- lized or partly desiccated (procedures to produce these partly desiccated organisms are given in WO2008/002371 ) or in form of spores.
• Microbial pesticides used as organism in an active state can be delivered in a growth medium without any additional additives or materials or in combination with suitable nutrient mixtures.
• microbial pesticides are delivered and formulated in a dormant stage, more preferably in form of spores.
• compositions which comprise a microbial pesticide as component 2
• the total weight ratios of compositions, which comprise a microbial pesticide as component 2 can be determined based on the total weight of the solid material (dry matter) of component 1 ) and using the amount of CFU of component 2) to calclulate the total weight of component 2) with the following equation that 1 x 10 9 CFU equals one gram of total weight of component 2).
• the compositions, which comprise a microbial pesticide comprise between 0.01 and 90% (w/w) of dry matter (solid material) of component 1 ) and from 1 x 10 5 CFU to 1 x 10 12 CFU of component 2) per gram total weight of the composition.
• compositions which comprise a microbial pesticide, comprise between 5 and 70% (w/w) of dry matter (solid material) of component 1 ) and from 1 x 10 6 CFU to 1 x 10 10 CFU of component 2) per gram total weight of the composition.
• the compositions, wherein one component is a microbial pesticide comprise between 25 and 70% (w/w) of dry matter (solid material) of component 1 ) and from 1 x 10 7 CFU to 1 x 10 9 CFU of component 2) per gram total weight of the composition.
• the application rates preferably range from about 1 x 10 6 to 5 x 10 15 (or more) CFU/ha.
• the spore concentration is about 1 x 107 to about 1 x 101 1 CFU/ha.
• (entomopathogenic) nematodes as microbial pesticides (e.g.
• the application rates preferably range inform about 1 x 10 5 to 1 x 10 12 (or more), more preferably from 1 x 10 8 to 1 x 10 11 , even more preferably from 5 x 10 8 to 1 x 10 10 individuals (e.g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.
• the application rates with respect to plant propagation material preferably range from about 1 x 10 6 to 1 x 10 12 (or more) CFU/seed.
• the concentration is about 1 x 10 6 to about 1 x 10 11 CFU/seed.
• the application rates with respect to plant propagation material also preferably range from about 1 x 10 7 to 1 x 10 14 (or more) CFU per 100 kg of seed, preferably from 1 x 10 9 to about 1 x 10 11 CFU per 100 kg of seed.
• the compounds of formula (I), or their stereoisomers, salts, tautomers and N-oxides may also be applied with fungicides as compound II.
• strobilurins azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb/chlorodincarb, tri- floxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2 (2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide;
• oxazolidinediones and imidazolinones famoxadone, fenamidone;
• Inhibitors of complex II e.g. carboxamides
• carboxanilides benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr, isofetamid, isopyrazam, isotianil, mepronil, oxycarboxin, pen- flufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5- carboxanilide, N-(3',4',5' trifluorobiphenyl-2 yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4 carbox- amide (fluxapyroxad), N-(4'-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1 -methyl-1 H pyra- zole-4-carboxamide, N-(
• Inhibitors of complex III at Qi site cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8-benzyl-3- [(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine- 2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)- 8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-
• respiration inhibitors diflumetorim; (5,8-difluoroquinazolin-4- yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine; tecnazen; ametoctradin; silthiofam; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, ferimzone; nitrthal- isopropyl, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
• triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, dinicona- zole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hex- aconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, pen- conazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triad- imefon, triadimenol, triticonazole, uniconazole, 1 -[re/-(2S;3R)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)-oxiranylmethyl]-5-thio
• imidazoles imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole;
• pyrimidines, pyridines and piperazines fenarimol, nuarimol, pyrifenox, triforine, [3-(4-chloro-2- fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol;
• morpholines aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;
• piperidines fenpropidin, piperalin; spiroketalamines: spiroxamine;
• phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, met- alaxyl-M (mefenoxam), ofurace, oxadixyl;
• isoxazoles and iosothiazolones hymexazole, octhilinone;
• F.IV Inhibitors of cell division and or cytoskeleton
• F.IV-1 Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuber- idazole, thiabendazole, thiophanate-methyl;
• triazolopyrimidines 5-chloro-7 (4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5 a]pyrimidine;

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