WO2014079820A1 - Utilisation de composés d'anthranilamides pour réduire les infections virales véhiculées par les insectes - Google Patents

Utilisation de composés d'anthranilamides pour réduire les infections virales véhiculées par les insectes Download PDF

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WO2014079820A1
WO2014079820A1 PCT/EP2013/074116 EP2013074116W WO2014079820A1 WO 2014079820 A1 WO2014079820 A1 WO 2014079820A1 EP 2013074116 W EP2013074116 W EP 2013074116W WO 2014079820 A1 WO2014079820 A1 WO 2014079820A1
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compound
formula
plant
group
alkyl
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PCT/EP2013/074116
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Karsten KÖRBER
Jean-Yves WACH
Florian Kaiser
Matthias Pohlman
Prashant Deshmukh
Deborah L. Culbertson
W. David ROGERS
Koshi Gunjima
Michael David
Franz Josef Braun
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Basf Se
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to new uses and methods of reducing insect-vectored viral infection and transmission in plants, methods of reducing damage to plants caused by viral infection, methods of crop enhancement including methods for improving plant growth, vigour and yield, by application of N-thio-anthranilamide compounds, and their mixtures with selected other pesticides.
  • the agrochemical industry is continually seeking methods of controlling plant pests and improving the growth of plants.
  • Chemicals are typically used (i) to control undesirable species (for example, pests, such as insects, or vegetation, e.g., weeds, or fungi), and (ii) to promote plant growth (e.g., by providing nutrients), and thereby improve the growth of plants.
  • Insect-vectored viral infections are a widespread cause of plant damage, for which there are few effective measures of control.
  • 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 describes N-thio-anthranilamide compounds with a sulfilimine or sulfoximine group and their use as pesticides.
  • PCT/EP2012/065649 and EP1 1 189973.8 describe processes for the synthesis of N-Thio- anthranilamide compounds.
  • International patent applications WO 2008/021 152 and WO 2008/122396 refer to the use of certain anthranilamides for increasing crop vigour and yield.
  • International patent application WO 2008/020998 refers to the in-furrow fungicide application for reducing plant damage by control of insect-vectored viral infection.
  • International patent application WO201 1/134876 decribes methods for reducing insect-vectored viral infections by application of a combination of certain insecticides, i.a. anthranilic bis-amides, and a plant activator.
  • anthranilamide compounds of formula (I) are suitable for reducing insect-vectored viral infection in a plant, reducing insect-vectored-viral transmission amongst plants, and reducing damage to a plant caused by one or more insect-vectored viral infections.
  • the present invention relates to the use of at least one pesticidally active anthranilamide compound of formula (I): wherein
  • R 1 is selected from the group consisting of halogen, methyl and halomethyl
  • 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 4 is hydrogen or halogen
  • R 5 , 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
  • R b is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3- Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein one or more CH2 groups of the last four radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from 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, R b is selected from the group consisting of Ci-C6-alkyl, C2-C6
  • phenyl, benzyl, pyridyl and phenoxy wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (C1-C6- alkoxy)carbonyl;
  • the invention relates to a method of reducing insect-vectored viral infection in a plant by application of at least one pesticidally active anthranilamide compound of formula (I) as defined above.
  • mixtures of compounds of formula I, or a stereoisomer, salt, tautomer or N-oxide thereof, with other selected pesticides are highly suitable in the use for reducing insect- vectored viral infection in a plant, or reducing insect-vectored-viral transmission amongst plants, or reducing damage to a plant caused by one or more insect-vectored viral infections, and the respective methods by application of at least one pesticidally active anthranilamide compound of formula (I).
  • 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 organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
  • partially or fully halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • a partially or fully halogenated radical is termed below also “halo- radical”.
  • partially or fully halogenated alkyl is also termed haloalkyl.
  • alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyi) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 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.
  • Examples of CrC 4 -alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl,
  • Ci-Cio-alkyl are, apart those mentioned for CrC 6 -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-Ci 0 -haloalkyl”), frequently from 1 to 6 carbon atoms (“Ci-C 6 -haloalkyl”), more frequently 1 to 4 carbon atoms (“Ci-Ci 0 -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
  • haloalkyl moieties are selected from CrC 4 -haloalkyl, more preferably from CrC 2 -haloalkyl, more preferably from halome- thyl, in particular from CrC 2 -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.
  • CrC 2 -fluoroalkyl examples include fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like.
  • Examples for CrC 2 -haloalkyl are, apart those mentioned for d- C 2 -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-C 4 -haloalkyl are, apart those mentioned for Ci-C 2 - haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trif I uoroprop-2-y 1 , 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 bicydic cycloaliphatic radical having usually from 3 to 10 carbon atoms ("C 3 -Cio-cycloalkyl”), preferably 3 to 8 carbon atoms (“C 3 -C8-cycloalkyl”) or in particular 3 to 6 carbon atoms ("C 3 -C 6 - 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.
  • Examples of 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.
  • halocydoalkyi as used herein (and in the halocydoalkyi moieties of other groups comprising an halocydoalkyi 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 hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine.
  • Examples are 1 - and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3- tetrafluorocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2- trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1 -,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 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.
  • C 3 -C 8 -cycloalkyl-Ci- C 4 -alkyl refers to a C 3 -C 8 -cycloalkyl group as defined above which is bound to the remainder of the molecule via a CrC 4 -alkyl group, as defined above.
  • Examples are cyclopropylmethyl, cyclo- propylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutyl propyl, cyclopen- tylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexyl propyl, and the like.
  • alkenyl denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 10 (“C 2 -Cio-alkenyl”), preferably 2 to 6 carbon atoms (“C2-C 6 -alkenyl”), in particular 2 to 4 carbon atoms (“C 2 -C 4 -alkenyl”), and a double bond in any position, for example C 2 -C 4 -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; C 2 -C 6 -alkenyl, such as ethenyl, 1 -propenyl, 2- propen
  • 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 (“C 2 -Cio-alkynyl”), frequently 2 to 6 (“C 2 -C 6 -alkynyl”), preferably 2 to 4 carbon atoms (“C 2 -C 4 -alkynyl”) and one or two triple bonds in any position, for example C 2 - C 4 -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C 2 -C 6 -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like
  • 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 ("C 2 -Ci 0 -haloalkynyl”), frequently 2 to 6 (“C 2 -C 6 -haloalkynyl”), preferabyl 2 to 4 carbon atoms (“C 2 -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.
  • alkoxy denotes in each case a straight-chain or branched alkyl group usually having from 1 to 10 carbon atoms ("Ci-Ci 0 -alkoxy”), frequently from 1 to 6 carbon atoms (“CrC 6 -alkoxy”), preferably 1 to 4 carbon atoms (“CrC 4 -alkoxy”), which is bound to the remainder of the molecule via an oxygen atom.
  • Ci-C 2 -Alkoxy is methoxy or ethoxy.
  • d-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).
  • CrC 6 -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,
  • CrC 8 -Alkoxy is addition- ally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • C-i-C-io- 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-Ci 0 -haloalkoxy”), frequently from 1 to 6 carbon atoms (“CrC 6 -haloalkoxy”), preferably 1 to 4 carbon atoms (“CrC 4 - haloalkoxy”), more preferably 1 to 3 carbon atoms (“CrC 3 -haloalkoxy”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
  • C C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHCI 2 , 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 OC 2 F 5.
  • Ci-C 4 -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, OCH 2 -C 2 F 5 , OCF 2 -C 2 F 5 , 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.
  • CrC 6 -Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
  • alkoxyalkyl denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 10, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Ci-C 6 -Alkoxy-Ci-C 6 -alky is a CrC 6 -alkyl group, as defined above, in which one hydrogen atom is replaced by a CrC 6 -alkoxy group, as defined above.
  • Examples are CH 2 OCH 3 , CH 2 - OC 2 H 5 , n-propoxymethyl, CH 2 -OCH(CH 3 ) 2 , n-butoxymethyl, (l -methylpropoxy)-methyl, (2- methylpropoxy)methyl, CH 2 -OC(CH 3 ) 3 , 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2- (1 -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1 -methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-
  • 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 - difluoroethoxy methyl, 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 (“CrCio-alkylthio”), frequently comprising 1 to 6 carbon atoms (“CrC 6 -alkylthio”), preferably 1 to 4 carbon atoms (“Ci-C 4 -alkylthio”), which is attached via a sulfur atom at any position in the alkyl group.
  • CrC 2 -Alkylthio is methylthio or ethylthio.
  • Ci-C 4 -Alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec- butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio).
  • CrC 6 - Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3- methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1 - ethylpropylthio, hexylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4- methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2- dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,1
  • CrC 8 -Alkylthio is additionally, for example, heptylthio, octylthio, 2- ethylhexylthio and positional isomers thereof.
  • Ci-Ci 0 -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.
  • CrC 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-dichloro
  • 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.
  • CrC 2 -alkylsulfinyl refers to a CrC 2 -alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C C 4 -alkylsulfinyl refers to a Ci-C 4 -alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 6 -alkylsulfinyl refers to a CrC 6 -alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -alkylsulfinyl is methylsulfinyl or ethyl- sulfinyl.
  • Ci-C 4 -alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl).
  • CrC 6 -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-dimethylbutylsulfin
  • 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.
  • the term "Ci-C 2 - alkylsulfonyl” refers to a CrC 2 -alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • C C4-alkylsulfonyl refers to a CrC 4 -alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • C C6-alkylsulfonyl refers to a CrC 6 -alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C 2 -alkylsulfonyl is methylsulfonyl or ethyl- sulfonyl.
  • d-C 4 -alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2- methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl).
  • CrC 6 - alkylsulfonyl is additionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl, 2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2- dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 - methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1 ,1 -dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1 ,3-dimethylbutylsulf
  • alkylamino denotes in each case a group -NHR, wherein R is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms ("Ci-C 6 - alkylamino"), preferably 1 to 4 carbon atoms("Ci-C 4 -alkylamino").
  • Ci-C 6 -alkylamino examples are 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-C 6 -alkyl)-amino"), preferably 1 to 4 carbon atoms (“di-(CrC 4 - alkyl)-amino").
  • Examples of a di-(Ci-C 6 -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 ("C 3 -C 8 -cycloalkylamino"), preferably 3 to 6 carbon atoms("C 3 -C 6 -cycloalkylamino").
  • C 3 -C 8 -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.
  • Preparation of the compounds of formula I can be accomplished according to standard methods of organic chemistry, e.g. by the methods or working examples described in WO 2007/006670, PCT/EP2012/065650 and PCT/EP2012/065651 , without being limited to the routes given therein.
  • 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.
  • Agronomically acceptable salts of the compounds I can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
  • R 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. Preferred are methods and uses of compounds of formula (I), in which the compound of formula I is a compound of formula IC:
  • 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 independently of one another from the group consisting of hydrogen, Ci-Cio-alkyl, Cs-Cs-cycloalkyI, 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
  • R 7 is selected from the group consisting of bromo, difluoromethyl, trifluoromethyl and OCHF2.
  • 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 invention 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 2 Compounds of the formula (IA-1 ) in which R 1 is Br, 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 3 Compounds of the formula (IA-1 ) in which R 1 is CI, R 2 is CI, R 7 is CF 3 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 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 12 Compounds of the formula (IA-1 ) in which R 1 is methyl, 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 13 Compounds of the formula (IA-1 ) in which R 1 is F, 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 17 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is Br, R 7 is CHF2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
  • Table 18 Compounds of the formula (IA-1 ) in which R 1 is Br, 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 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 CHF2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
  • Table 21 Compounds of the formula (IA-1 ) in which R 1 is F, R 2 is cyano, R 7 is CHF2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A;
  • Table 22 Compounds of the formula (IA-1 ) in which R 1 is Br, R 2 is cyano, R 7 is CHF2 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 33 Compounds of the formula (IA-1 ) in which R 1 is F, 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 34 Compounds of the formula (IA-1 ) in which R 1 is Br, 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 47 Compounds of the formula (IA-1 ) in which R 1 is CI, 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 48 Compounds of the formula (IA-1 ) in which R 1 is methyl, 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 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;
  • Table 60 Compounds of the formula (IA-1 ) in which R 1 is methyl, 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 A Compounds of the formula (IA-1 ) in which R 1 is methyl, 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-103 CH CH 2 CH(CH 3 ) 2 A-145 c-C 6 Hii CH 2 CH 2 CH 2 CH 3
  • A-1 18 C-C4H7 CH(CH 3 ) 2 A-160 CH 2 CH CH 2 C(CH 3 ) 3
  • A-1 19 C-C5H9 CH(CH 3 ) 2 A-161 CH 2 C ⁇ CH C(CH 3 ) 3
  • A-178 CH CH 2 CH 2 CH(CH 3 ) 2
  • A-203 CH CH 2 CH(CH 3 )CH 2 CH 3
  • A-245 c-C 6 Hii CH 2 CH CH 2
  • A-260 CH 2 CH CH 2 CH 2 C ⁇ CH A-302 C2H5 CHF 2
  • A-460 CH 2 CH CH 2 C-C5H9 A-502 C2H5 CH 2 -c-C 3 H 5 R 5 R 6 R 5 R 6
  • A-610 CH 2 CH CH 2 C6H5 A-652 C2H5 CH 2 CH 2 -c-C 3 H 5
  • A-628 CH CH 2 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; C6H 5 : phenyl;
  • CH2CH2-C-C3H5 2-cyclopropylethyl
  • CH2-C-C4H7 2-cyclobutylmethyl
  • 2-EtHex 2-etHex:
  • 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 accordance with Table C of the example section:
  • 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 method is connected with controlling hemiptera, preferably aphids or whitefly.
  • Plants exhibiting aphid damage can have a variety of symptoms, such as decreased growth rates, mottled leaves, yellowing, stunted growth, curled leaves, browning, wilting, low yields and death.
  • the removal of sap creates a lack of vigour in the plant, and aphid saliva is toxic to plants.
  • Hemiptera, in particular aphids frequently transmit disease- causing organisms like plant viruses to their hosts.
  • the green peach aphid (Myzus persicae) is a vector for more than 1 10 plant viruses.
  • Cotton aphids (Aphis gossypii) often infect sugarcane, papaya and groundnuts with viruses. Aphids contributed to the spread of late blight (Phytophthora in- festans) among potatoes in the Great Irish Potato Famine of the 1840s.
  • the cherry aphid or black cherry aphid, Myzus cerasi, is responsible for some leaf curl of cherry trees. This can easily be distinguished from 'leaf curl' caused by Taphrina fungus species due to the presence of aphids beneath the leaves.
  • honeydew The coating of plants with honeydew can contribute to the spread of fungi which can damage plants.
  • Honeydew produced by aphids has been observed to reduce the effectiveness of fungicides as well.
  • the neonicotinoids represent the fastest-growing class of insecticides introduced to the market since the commercialization of pyrethroids (Nauen and Denholm, 2005: Archives of Insect Biochemistry and Physiology 58:200-215) and are extremely valuable insect control agents not least because they had exhibited little or no cross-resistance to the older insecticide classes, which suffer markedly from resistance problems
  • the invention also provides a method of protecting a crop of useful plants, from virus infection. Such a method involves applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insects, a compound of formula I.
  • the method of reducing insect-vectored viral infection in a plant is not connected to the ability of a compound of formula I to control insects, in particular aphids.
  • the method of reducing insect-vectored viral infection in a plant is especially surprisingly effective if the compound of formula I in question is not effective, or not very effective, or not sufficiently effective in the control of insects (e.g. aphids).
  • the compound of formula I may be used in a resistance management strategy with a view to controlling resistance to the neonicotinoid class of insecticides.
  • a resistance management strategy may involve alternating applications of a compound of formula I and a neonicotinoid insecticide, either on an application by application alternation (including different types of application, such as treatment of plant propa- gation material and foliar spray), or seasonal/crop alternation basis (e.g. use a compound of formula I on a first crop/for control in a first growing season, and use a neonicotinoid insecticide for a subsequent crop/growing season, or vice versa), and this forms yet a further aspect of the invention.
  • application alternation including different types of application, such as treatment of plant propa- gation material and foliar spray
  • seasonal/crop alternation basis e.g. use a compound of formula I on a first crop/for control in a first growing season, and use a neonicotinoid insecticide for a subsequent crop/
  • a further aspect of the invention provides a method of controlling a plant virus in a crop of useful plants susceptible to and/or under attack by neonicotinoid resistant insects which carry said plant virus, which method comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insects, a compound of formula I.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Sobemovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Caulimovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Closterovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Sequivirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Enamovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Luteovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Polerovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Umbravirus. In one embodiment, the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Nanovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Cytorhabdovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound of formula I, wherein the virus is Nucleorhabdovirus.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is soybean.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is rice.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is cotton.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is oilseed rape.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is peanut.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is cereal.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is wheat.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is barley.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is corn.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is a specialty crop.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is fruiting vegetable. In one embodiment, the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is leafy vegetable.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is tomato.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is pepper.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is eggplant.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is cabbage.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is lettuce.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is potatoes.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is onions.
  • the invention relates tothe a use or method for reducing insect-vectored viral infection in a plant or crop, which method comprises applying a compound of formula I, wherein the plant or crop is tobacco.
  • the invention relates to a use or method for reducing insect-vectored viral infection in a plant, 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, the invention relates to a use or method for reducing insect-vectored viral infection in a plant, which method comprises applying a compound 1-1 1. Analogously, the invention relates to a use or method as explained, applying specifically compound 1-16. Analogously, the invention relates to a use or method as explained, applying specifically compound 1-16.
  • the invention relates to a use or method as explained, applying specifically compound 1-21. Analogously, the invention relates to a use or method as explained, applying specifically compound I-26. Analogously, the invention relates to a use or method as explained, applying specifically compound 1-31 .
  • the invention relates to a use or method for reducing insect- vectored viral infection in a plant/crop, wherein the virus and the plant/crop is as defined in entries VC-1 to VC-224 of Table VC, 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 invention relates to a use or method for reducing insect-vectored viral infection in a plant/crop, wherein the virus and the plant/crop is as defined in entries VC-1 to VC-224 of Table VC, which method comprises applying a compound 1-1 1. Analogously, the invention relates to a use or method as explained, applying specifically compound 1-16.
  • the invention relates to a use or method as explained, applying specifically compound 1-16. Analogously, the invention relates to a use or method as explained, applying specifically compound 1-21 . Analogously, the invention relates to a use or method as explained, applying specifically compound I-26. Analogously, the invention relates to a use or method as explained, applying specifically compound I- 31 .
  • insects which are one or more of as an example Acyrthosiphum pisum, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis frangulae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Eriosoma lanigerum, Hyalopterus pruni, Lipaphis erysimi, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphum rosae, Myzus cerasi F., Myzus nicotianae, Myzus per- s
  • Methods of the invention as described herein may also involve a step of assessing whether insects are resistant to neonicotinoid insecticides and/or whether said insects carry a plant virus.
  • This step will in general involve collecting a sample of insects from the area (e.g. crop, field, habitat) to be treated, before actually applying a compound of formula I, and testing (for example using any suitable phenotypic, biochemical or molecular biological technique applicable) for resistance/sensitivity and/or the presence or absence of a virus.
  • the active agents of the invention may be applied as sole ingredients, or alternatively, each agent may be in the form of an agrochemical composition comprising an agrochemically acceptable diluent or carrier. References herein to the active agents of the invention or components comprising said agents shall be deemed to include the agents as sole ingredients or agrochemical compositions thereof.
  • the active agents of the invention may be applied simultaneously, separately or sequentially. Each active agent may be applied directly as separate components or as a mixture of the two.
  • 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 according to the present invention comprise the compound(s) as defined herein as well as a known 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 pesticidallyactive compound(s) II for being used and/or ap- plied in methods according to the invention as defined above.
  • the compounds of formula I and/or their mixtures of the present invention, their stereoisomers, their salts or their N-oxides, are particularly useful for being applied in methods for soil application methods for controlling invertebrate pests, in particular for controlling insects, arthropods and nematodes and especially (spider) mites. Therefore, the invention relates to the use of compounds of formula I and/or their mixtures, for combating or controlling invertebrate pests, in particular invertebrate pests of the group of insects, arachnids or nematodes.
  • the present invention relates further to a composition comprising at least one compound of formula I and/or its mixtures, including a stereoisomer, salt, tautomer or N-oxide thereof, and at least one inert liquid and/or solid carrier.
  • the invention relates to an agricultural composition comprising at least one compound of formula I and at least one liquid and/or solid carrier for use in the methods of the present invention.
  • pesticidally active compounds II with which the compounds of formula I are combined with for the methods according to present invention are the following:
  • the compounds of formula I can be combined and used in mixture with another pesticidally active compound (II) and applied in agriculture.
  • another pesticidally active compound (II) is active against said soil-living arthropod pest.
  • a skilled person is familiar with such compounds and knows which compounds are active against a specific target organism.
  • the compound (II) pesticides together with which the compounds of formula I may be used according to the purpose of the present invention, and with which potential synergistic effects with regard to the method of uses might be produced, are selected and grouped according to the Mode of Action Classification from the Insecticde Resistance Action Committee (IRAC) and are selected from group M consisting of
  • Acetylcholine esterase (AChE) inhibitors from the class of
  • organophosphates including acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disul- foton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyamino- thio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methoxyamino-
  • II-M.2A cyclodiene organochlorine compounds including endosulfan or chlordane; or II-M.2B fiproles (phenylpyrazoles), including ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
  • II-M.3A pyrethroids including acrinathrin, allethrin, d-cis-trans allethrin, d-trans alle- thrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cy- cloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, f
  • Nicotinic acetylcholine receptor agonists from the class of
  • II-M.8B chloropicrin or II-M.8C sulfuryl fluoride, or
  • II-M.1 Microbial disruptors of insect midgut membranes, including bacillus thurin- giensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thu- ringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp.
  • Cry1 Ab Cry1 Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
  • ll-M 12 Inhibitors of mitochondrial ATP synthase including
  • ll-M 12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or ll-M 12C propargite, or
  • Inhibitors of the chitin biosynthesis type 1 including buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, including methoxyfeno- zide, tebufenozide, halofenozide, fufenozide or chromafenozide; II-M.19 Octopamin receptor agonists, including amitraz;
  • Mitochondrial complex III electron transport inhibitors including
  • acaricides and insecticides such as fenazaquin, fenpyroximate, pyrim- idifen, pyridaben, tebufenpyrad or tolfenpyrad, or
  • Inhibitors of the acetyl CoA carboxylase including Tetronic and Tetramic acid derivatives, including spirodiclofen, spiromesifen or spirotetramat;
  • phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or
  • Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, including cyenopyrafen or cyflumetofen;
  • N2-(1 -methyl-2-methylsulfonylethyl)phthalamid or the compound ll-M.26.3: 3-bromo-N- ⁇ 2-bromo-4-chloro-6-[(1 -cyclopropylethyl)carbamoyl]phenyl ⁇ -1 -(3- chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide (proposed ISO name: cyclaniliprole), or the compound
  • ll-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 ll-M.26.5a) to ll-M.26.5d):
  • II-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;
  • ll-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;
  • ll-M.26.5c 5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2- pyridyl)pyrazole-3-carboxamide;
  • ll-M.26.6 N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)-3-iodo-phthalamide; or ll-M.26.7: 3-chloro-N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)phthalamide; ll-M.X insecticidal active compounds of unknown or uncertain mode of action, including afidopyropen, azadirachtin, amidoflumet, benzoximate, bifenazate, bromo- propylate, chinomethionat, cryolite, dicofol, flufenerim, flometoquin, fluensul- fone, flupyradifurone, piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumide or the compounds
  • ll-M.X.6a (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • ll-M.X.6b (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;
  • ll-M.X.6c (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide
  • ll-M.X.6d (E/Z)-N-[1 -[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • ll-M.X.6e (E/Z)-N-[1 -[1 -(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • ll-M.X.6f (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide
  • ll-M.X.7 triflumezopyrim; or -M.X.8: 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-
  • 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 granulosis virus, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium (formerly Verticillium lecanii), Metarhizium an- isopliae, M.
  • 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 II- M.X.1 has been described in WO2005/085216, II-M.X.8 in WO2009/002809 and in
  • the pyripyropene derivative II-M.X.2 has been described in WO 2006/129714.
  • the spiroketal-substituted cyclic ketoenol derivative II-M.X.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ke- toenol derivative II-M.X.4 from WO2008/06791 1 .
  • Triazoylphenylsulfide like II-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
  • Cyantraniliprole (Cyazypyr) is known from e.g. WO 2004/067528.
  • the phthalamides ll-M.26.1 and ll-M.26.2 are both known from WO 2007/101540.
  • the anthranilamide ll-M.26.3 has been described in WO 2005/077934.
  • the hydrazide compound ll-M.26.4 has been described in WO 2007/043677.
  • the anthranilamide ll-M.26.5a) is described in WO201 1/085575, the ll-M.26.5b) in WO2008/134969, the ll-M.26.5c) in US201 1/046186 and the ll-M.26.5d in WO2012/034403.
  • the diamide compounds ll-M.26.6 and ll-M.26.7 can be found in CN102613183.
  • the mesoionic antagonist compound II-M.X.9 was described in WO2012/0921 15, the nemati- cide II-M.X.10 in WO2013/055584 and the Pyridalyl-type analogue II-M.X.12 in
  • biopesticides from group ll-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, Germany), 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. BOTECTOR® from bio-ferm
  • Azospirillum brasilense XOH e.g. AZOS from Xtreme Gardening, USA USA or RTI Reforestation Technologies International; USA
  • Bacillus amyloliquefaciens IT-45 CNCM I 3800, NCBI 1091041 ) (e.g. RHIZOCELL C from ITHEC, France)
  • B. amyloliquefaciens subsp. plantarum MBI600 NRRL B-50595, deposited at United States Department of Agriculture
  • B. pumilus QST 2808 (NRRL Accession No. B 30087) (e.g.
  • 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. amyloliquefaciens D747 e.g.
  • BROAD-- BAND® 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 1-82 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 J1446: 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 J1446: 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. METATHR POL 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 Industries, 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. 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.
  • 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. ROOT PRO® from Mycontrol Ltd., Israel
  • 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. TRICHOPEL from Agrimm Technologies Ltd, NZ
  • T. TRICHOPEL from Agrimm Technologies Ltd, NZ
  • T. TRICHOPEL from Agrimm Technologies Ltd, NZ
  • T. TRICHOPEL from Agrimm Technologies Ltd, NZ
  • T. TRICHOPEL from Agrimm Technologies Ltd, NZ
  • T. viride ICC080 e.g. REMEDIER® WP from Isagro Ricerca, Italy
  • T. polysporum and T. harzi- anum e.g. BINAB® from BINAB Bio-Innovation AB, Sweden
  • T. stromaticum e.g. TRICO- VAB® from C.E.P.L.A.C., Brazil
  • T. virens GL-21 also named Gliocladium virens
  • SOIL- GARD® from Certis LLC, USA
  • T. viride e.g. TRIECO® from Ecosense Labs. (India) Pvt.
  • T. viride TV1 e.g. T. viride TV1 from Agribiotec srl, Italy
  • Ulocladium oudemansii HRU3 e.g. BOTRY-ZEN® from Botry-Zen Ltd, NZ
  • 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)
  • 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.
  • Bacillus subtilis 1430 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. in US 2012/0149571 A1 .
  • This strain MBI600 is commercially available as liquid formulation product Integral® (Becker-Underwood Inc., USA). Recently, the strain MBI 600 has been reclassified as Bacillus amyloliquefaciens subsp. plantarum based on polyphasic testing which combines classical microbiological methods relying on a mixture of traditional tools (such as culture-based methods) and molecular tools (such as genotyping and fatty acids analysis). Thus, 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 ll-M.Y-1 to ll-M.Y-2:
  • ll-M.Y-1 Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity:
  • the at least one biopesticide II is selected from group ll-M.Y-1 .
  • the at least one biopesticide II is se- lected from ll-M.Y-2.
  • the at least one biopesticide II is Bacillus 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. japonicum).
  • 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. Belts- ville 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. described 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, depos- ited 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.

Abstract

La présente invention concerne des procédés agricoles utilisant des composés d'anthranilamides de formule (I), R1, R2, R3, R4, R5, R6, R7 et k étant définis dans la description; ainsi que leurs mélanges. Les composés d'anthranilamides de formule (1) conviennent tout particulièrement pour des procédés visant à réduire les infections virales véhiculées par les insectes et leur transmission chez les plantes, et pour des procédés d'amélioration des récoltes, notamment des procédés visant à améliorer la croissance, la vigueur et le rendement des plantes, par application d'une combinaison d'un insecticide à base de bis-amide anthranilique ou d'un aminothiadiazole (modulateur de récepteurs de la ryanodine) et d'un activateur de plantes, à des compositions comportant les combinaisons et à du matériau de multiplication de plantes traité avec ceux-ci.
PCT/EP2013/074116 2012-11-22 2013-11-19 Utilisation de composés d'anthranilamides pour réduire les infections virales véhiculées par les insectes WO2014079820A1 (fr)

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US9765052B2 (en) 2013-02-20 2017-09-19 Basf Se Anthranilamide compounds, their mixtures and the use thereof as pesticides
CN108558761A (zh) * 2018-05-21 2018-09-21 青岛清原化合物有限公司 一种三唑磺草酮-水杨酸共晶及其制备方法和应用
WO2019123194A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation
WO2019123195A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Pyrazolopyridine-diamides, leur utilisation en tant qu'insecticide et leurs procédés de préparation
WO2019150220A1 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation

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EP3069610A4 (fr) * 2013-11-13 2017-04-12 Nippon Soda Co., Ltd. Co-cristal et son procédé de production
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