WO2019211106A1 - Lutte contre des nuisibles des plants de soja avec des composés méso-ioniques - Google Patents

Lutte contre des nuisibles des plants de soja avec des composés méso-ioniques Download PDF

Info

Publication number
WO2019211106A1
WO2019211106A1 PCT/EP2019/060141 EP2019060141W WO2019211106A1 WO 2019211106 A1 WO2019211106 A1 WO 2019211106A1 EP 2019060141 W EP2019060141 W EP 2019060141W WO 2019211106 A1 WO2019211106 A1 WO 2019211106A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
group substituted
spp
phenyl
Prior art date
Application number
PCT/EP2019/060141
Other languages
English (en)
Inventor
Ashokkumar Adisechan
Rizwan Shabbir SHAIKH
Devendra VYAS
Rupsha Chaudhuri
Pulakesh MAITY
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of WO2019211106A1 publication Critical patent/WO2019211106A1/fr

Links

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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the invention relates to a method for controlling pests of soybean plants, comprising the step of contacting the plant, parts of it, its propagation material, the pests, their food supply, habitat or breeding grounds with one or more compounds of formula I
  • R 1 represents R a or a Ci-alkyl group (where the Ci-alkyl group is substituted with one or more R a );
  • R 2 represents a phenyl group substituted with up to 3 R b ;
  • R 3 represents R a , a Ci-C 6 -alkyl group
  • Ci-C 6 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 6 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 6 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 6 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 6 -alkylsulfonyl group substituted with one or more R a , and/or
  • amino group has 2 substituent groups independently selected from hydrogen atom, Ci-C 4 -alkyl group, and C 2 -acyl group,
  • Ci-C 4 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a ,
  • Ci-C 4 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a and/or a Ci-C 3 -alkylsulfonyl group substituted with one or more R a ), and/or
  • heterocyclic group substituted with one or more R b (where the heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms,
  • heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 het- eroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitro- gen atom and sulfur atom);
  • R 4 represents R a , a Ci-C 6 -alkyl group
  • Ci-C 6 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a
  • Ci-C 6 -alkylthio group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a
  • amino group (where the amino group has 2 substituent groups independently selected from hydrogen atom, Ci-C 4 -alkyl group, and C 2 -C 6 -acyl group,
  • Ci-C 4 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a ,
  • Ci-C 4 -alkylthio group Ci-C 4 -alkylsufoxy group, or Ci-C 4 -alkylsufonyl group
  • Ci-C 4 -alkylthio group, Ci-C 4 -alkylsufoxy group, and Ci-C 4 -alkylsufonyl group are substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a );
  • R 5 represents a Ci-C 4 -alkyl group substituted with one or more R a , a C 2 -C 4 -alkenylene group substituted with one or more R a , or a C 2 -C 4 -alkynylene group substituted with one or more R a ;
  • each R b is independently selected from R a , pentafluorosulfanyl group, Ci-C 6 -alkyl group (where the Ci-C 6 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a
  • Ci-C 6 -alkyloxy group
  • Ci-C 6 -alkyloxy group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a
  • amino group has 2 substituent groups independently selected from hydrogen atom, Ci-C 4 -alkyl group, and C 2 -acyl group,
  • Ci-C 4 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a and/or a Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a ,
  • Ci-C 4 -alkylthio group Ci-C 4 -alkylsulfoxy group
  • Ci-C 4 -alkylthio group, Ci-C 4 -alkylsulfoxy group, and Ci-C 4 -alkylsulfonyl group are substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a
  • each R c is independently selected from R a , Ci-C 4 -alkyl group, C 2 -C 3 -alkenyl group, C 2 - C 3 -alkynyl group, C 3 -C 6 -cycloalkyl group, Ci-C 6 -alkyloxy group, Ci-C 4 -alkylthio group, C 1 - C 4 -alkylsulfoxy group, Ci-C 4 -alkylsulfonyl group, phenyl group, heterocyclic group
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 het- eroatoms
  • heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom
  • Ci-C 4 -alkyl group C 2 -C 3 -alkenyl group, C 2 -C 3 -alkynyl group, C 3 -C 6 -cycloalkyl group, Ci-C 6 -alkyloxy group, Ci-C 4 -alkylthio group, Ci-C 4 -alkylsulfoxy group, Ci-C 4 -alkyl- sulfonyl group, phenyl group, and heterocyclic group are substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylthio group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with one or more R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with one or more R a
  • the above compounds can be used in pure form or as mixtures.
  • the compounds of formula I can be prepared by methods disclosed in the patent publication WO2018062082.
  • the organic moieties mentioned in the definition of the variables R a , R b , R c , R 1 , R 2 , R 3 , R 4 and R 5 are - like the term halogen - collective terms for individual enumerations of the individual group members.
  • the term halogen denotes in each case F, Cl, Br, or I.
  • All hydrocarbon chains, e.g. all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
  • Ci-C 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
  • Ci-C4-haloalkyl Ci-C 4 -alkyl as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluo- romethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethy
  • Ci-C 4 -alkoxy e.g. methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2- methylpropoxy, and 1 ,1-dimethylethoxy;
  • Ci-C 4 -haloalkoxy a Ci-C 4 -alkoxy group as mentioned above which is partially or fully sub- stituted with fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,
  • C 2 -C 6 -alkenyl e.g. ethynyl, 1-propenyl, and 2-propenyl;
  • C 3 -C 6 -haloalkenyl a C 3 -C 6 -alkenyl substituent as mentioned above which is partially or fully substituted with fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1-yl, and 3-chloroprop-2-en-1 -yl;
  • C 2 -C 6 -alkynyl e.g. ethynyl, 1-propynyl, and 2-propynyl;
  • C 2 -C 6 -haloalkynyl a C 2 -C 3 -alkynyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I, e.g. 1 ,1-difluoroprop-2-yn-1-yl, and 3-chloroprop-2-yn-1-yl;
  • Ci-C 6 -alkylthio e.g. methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1- methylpropylthio, 2-methylpropylthio, and 1 , 1 -dimethylethylthio;
  • Ci-C 6 -haloalkylthio Ci-C 4 -alkylthio group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I;
  • Ci-C 6 -haloalkylsulfinyl Ci-C 4 -alkylsulfinyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I;
  • Ci-C 6 -alkylsulfonyl (Ci-C 4 -alkyl-S(0) 2 -): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, and 1 -methylethylsulfonyl;
  • Ci-C 6 -haloalkylsulfonyl Ci-C4-alkylsulfonyl group as mentioned above which is partially or fully substituted with F, Cl, Br and/or I;
  • heterocyclyl a 3- to 8-membered heterocyclyl: a saturated or partially or fully un- saturated cycle having three to eight ring members comprising 2-6 carbon atoms and 1 -2 het- eroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom, or comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
  • 6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
  • heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an ox ygen or a sulfur atom, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g.
  • pyrazol-3-yl, pyra- zol-4-yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g.
  • thiazol-2-yl thiazol-4-yl, thiazol-5-yl
  • oxadia- zolyl e.g. 1 ,2,3-oxadiazol-4-yl, 1 ,2,3-oxadiazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl,
  • thiadiazolyl e.g. 1 ,2,3-thiadiazol-4-yl, 1 ,2,3-thiadiazol-5-yl, 1 ,2,4-thiadia- zol-3-yl, 1 ,2,4-thiadiazol-5-yl, 1 ,3,4-thiadiazolyl-2-yl
  • triazolyl e.g. 1 ,2,3-triazol-4-yl, 1 ,2,4-tria- zol-3-yl
  • 1 -tetrazolyl 6-membered aromatic rings like pyridyl (e.g.
  • pyridine-2 -yl pyridine-3-yl, pyridine-4-yl
  • pyrazinyl e.g. pyridazin-3-yl, pyridazin-4-yl
  • pyrimidinyl e.g. pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl
  • pyrazin-2-yl triazinyl (e.g. 1 ,3,5-triazin-2-yl, or 1 ,2,4— triazin-3-yl
  • substituted or“substituted with one or more” if not specified otherwise refers to sub- stituted with 1 , 2, or up to maximum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.
  • substituted with up to X refers to substituted with 0 to X, wherein X is number.
  • Faboideae such as soybeans (Glycine max) are important commercial crops.
  • Soybeans are considered to be a source of complete protein (Henkel, J., 2000, "Soy: Health Claims for Soy Protein, Question About Other Components”. FDA Consumer (Food and Drug Administration 34 (3): 18-20). For this reason, soy is a good source of protein. According to the US Food and Drug Administration, soy protein products can be good substitutes for animal products because soy offers a 'complete' protein profile. Soy protein products can replace ani- mal-based foods which also have complete proteins but tend to contain more fat, especially sat- urated fat without requiring major adjustments elsewhere in the diet. Soybean protein isolate is highly valuable as it has a biological value of 74 (Protein Quality Evaluation: Report of the Joint FAO/WHO Expert Consultation. Bethesda, MD (USA): Food and Agriculture Organization of the United Nations (Food and Nutrition Paper No. 51 , December 1989).
  • soybeans can produce at least twice as much protein per acre than some other major vegetable or grain crop, e.g. 5 to 10 times more protein per acre than land set aside for grazing animals to make milk, and up to 15 times more protein per acre than land set aside for meat production ("Soy Benefits", National Soybean Research Laboratory, February 2012).
  • soybeans can be regarded as a globally important crop providing oil and protein.
  • soybean plants are vulnerable to a wide range of bacterial diseases, fungal dis eases, viral diseases and parasites. Soybeans are considered to be e.g. the second-most valu- able agricultural export in the United States behind corn.
  • Stink bugs are animal pests and true bugs. They are probably one of the most common pest problems in soybean (Stewart et al., Soybean In- sects - Stink bugs, University of Tennessee Institute of Agriculture, W200 09-0098).
  • Stink bugs feed on over 52 plants, including native and ornamental trees, shrubs, vines, weeds, and many cultivated crops such as corn and cotton, as well as numerous uncultivated plants, and their preferred hosts are nearly all wild plants. They build up on these hosts and move to soybeans late in the season as their preferred foods mature.
  • Stink bugs may feed on many parts of the plant; however, they typically target developing seed including the pods, meaning that injury to soybean seed is the primary problem associated with stink bug infestations.
  • Brown or blackish spots may occur where their mouthparts penetrate the plant tissue, but little external signs of feeding injury may be present. Feeding may cause deformation, shriveling or abortion of small seed. Larger seed may only be partly discolored by feeding injury, but this can affect seed quality. High levels of seed abortion may cause the "green bean effect" where foli- age is retained and plant maturity is delayed (Stewart et al., Soybean Insects - Stink bugs, Uni- versity of Tennessee Institute of Agriculture, W200 09-0098).
  • Stink bugs inflict mechanical injury to the seed as well as transmitting the yeast-spot disease organism.
  • the degree of damage caused by this pest depends to some extent on the develop- mental stage of the seed when it is pierced by the stink bug's needlelike mouthparts. The younger the seed when damaged, the greater the yield reduction. Although late season infesta- tions may not affect yield, bean oil content and germination will be reduced.
  • the green stink bug (Acrosternum hilare) is one of the most common spe- cies that feeds on soybean.
  • the brown stink bug (Euschistus servus) is another common com- ponent of the stink bug complex.
  • Insecticides commonly used to control stinkbugs include pyrethroids, neonicotinoids and or- ganophosphates, though pyrethroid insecticides are usually the method of choice for controlling stink bugs in soybean.
  • pyrethroid insecticides are usually the method of choice for controlling stink bugs in soybean.
  • problems with insecticide resistance par- ticularly in brown stink bug populations and particularly to pyrethroids.
  • Euschistus heros can also be difficult to manage using organophosphates or endosulfan (Sosa-Gomez et al., 2009). There is therefore a need for effective ecological methods of controlling stinkbugs in soybean.
  • compounds of formula I provide an efficient control against pests on Faboideae, in particular soybeans, more particularly genetically modified soybeans, espe- cially against pests from the family of Pentatomidae, family of Agromyzidae, family of Sternor- rhyncha, order of Lepidoptera, and/or order of Thysanoptera, particularly against pests from the families of Pentatomidae, Noctuidae, Pyralidae, Agromyzidae, and Thripidae.
  • a method for controlling pests of Faboideae comprising the step of contacting the Faboideae, in particular soybean, plant, parts of it, its propagation material, the pests, their food supply, habi- tat or breeding grounds with one or more compounds of formula I.
  • a method for controlling pests from the family of Pentatomidae, family of Agromyzidae, family of Sternorrhyncha, order of Lepidoptera, and/or order of Thysanoptera comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Pentatomidae, Noctuidae, Pyralidae, Agromyzidae, and/or Thripidae comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Pentatomidae, Noctuidae, and/or Thripidae comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Pentatomidae, and/or Thripidae comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Pentatomidae comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Pentatomidae, and/or Noctuidae comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Noctuidae comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Thripidae comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I.
  • a method for controlling pests from the family of Faboideae plants comprising the step of contacting the pests, their food supply habitat and/or breeding ground with one or more compounds of formula I and mixtures comprising corn- pounds of formula I.
  • R 1 is a hydrogen atom or methyl group
  • R 1 is substituted at position 8;
  • R 2 is a phenyl group substituted with up to 3 R b ;
  • R 3 is R a , a Ci-C 6 -alkyl group
  • Ci-C 6 -alkyloxy group substituted with R a a Ci-C 6 -alkyloxy group substituted with R a , and/or
  • Ci-C 6 -alkylthio group substituted with R a , and/or
  • Ci-C 6 -alkylsulfoxy group substituted with R a , and/or
  • Ci-C 6 -alkylsulfonyl group substituted with R a , and/or
  • Ci-C 6 -alkylamino group a substituted with R a (having 2 substituent groups inde- pendently selected from hydrogen atom, Ci-C 4 -alkyl group and C2-acyl group), and/or
  • heterocyclic group substituted with R b (where the heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are in- dependently selected from oxygen atom, nitrogen atom and sulfur atom)), a C2-C6-alkenyl group
  • Ci-C 6 -alkyl group substituted with R a , and/or
  • Ci-C3-alkyloxy group substituted with R a , and/or
  • Ci-C3-alkylthio group substituted with R a a Ci-C3-alkylthio group substituted with R a , and/or
  • Ci-C3-alkylsulfoxy group substituted with R a , and/or
  • Ci-C3-alkylsulfonyl group substituted with R a a Ci-C3-alkylsulfonyl group substituted with R a
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom);
  • R 4 is R a , a Ci-C 6 -alkyl group
  • amino group (where the amino group has 2 substituent groups independently selected from hy- drogen atom, Ci-C 4 -alkyl group, and C 2 -acyl group,
  • Ci-C 4 -alkyl group is substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with R a a Ci-C 3 -alkyloxy group substituted with R a , and/or
  • Ci-C 3 -alkylthio group substituted with R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with R a
  • R 5 is a Ci-C 2 -alkyl group, alkenylene group or alkynylene group substituted with one or more R a ;
  • each R a is independently selected from hydrogen atom, halogen atom, cyano group, nitro group, and SCN group;
  • each R b is independently selected from R a , pentafluorosulfanyl group, Ci-C 6 -alkyl group, and Ci-C 6 -alkyloxy group
  • Ci-C 6 -alkyl group and Ci-C 6 -alkyloxy group are substituted with R a , and/or
  • each R c is independently selected from R a , Ci-C 4 -alkyl group, C 3 -C 6 -cycloalkyl group, and C 2 -acyl group
  • Ci-C 4 -alkyl group and the C 3 -C 6 -cycloalkyl are substituted with one or more R a , and/or
  • Ci-C 3 -alkyloxy group substituted with R a a Ci-C 3 -alkyloxy group substituted with R a , and/or
  • Ci-C 3 -alkylthio group substituted with R a , and/or
  • Ci-C 3 -alkylsulfoxy group substituted with R a , and/or
  • Ci-C 3 -alkylsulfonyl group substituted with R a
  • R 1 is a hydrogen atom or methyl group
  • R 2 is a phenyl group substituted with up to 3 R b ;
  • R 3 is R a , a Ci-C 6 -alkyl group
  • Ci-C 6 -alkyloxy group substituted with R a a Ci-C 6 -alkyloxy group substituted with R a , and/or
  • Ci-C 6 -alkylthio group substituted with R a , and/or
  • Ci-C 6 -alkylsulfoxy group substituted with R a , and/or
  • Ci-C 6 -alkylsulfonyl group substituted with R a and/or a Ci-C 6 -alkylamino group a substituted with R a (having 2 substituent groups inde- pendently selected from hydrogen atom, Ci-C4-alkyl group and C2-acyl group), and/or
  • heterocyclic group substituted with R b (where the heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are in- dependently selected from oxygen atom, nitrogen atom and sulfur atom)), a C2-C6-alkenyl group
  • Ci-C 6 -alkyl group substituted with R a , and/or
  • Ci-C3-alkyloxy group substituted with R a , and/or
  • Ci-C3-alkylthio group substituted with R a a Ci-C3-alkylthio group substituted with R a , and/or
  • Ci-C3-alkylsulfoxy group substituted with R a , and/or
  • Ci-C3-alkylsulfonyl group substituted with R a a Ci-C3-alkylsulfonyl group substituted with R a
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom);
  • R 4 is R a , a Ci-C 6 -alkyl group
  • amino group has 2 substituent groups independently selected from hy- drogen atom, Ci-C 4 -alkyl group, and C2-acyl group,
  • Ci-C 4 -alkyl group is substituted with one or more R a , and/or
  • Ci-C3-alkyloxy group substituted with R a , and/or
  • Ci-C3-alkylthio group substituted with R a a Ci-C3-alkylthio group substituted with R a , and/or
  • Ci-C3-alkylsulfoxy group substituted with R a , and/or
  • Ci-C3-alkylsulfonyl group substituted with R a
  • R 5 is a Ci-C2-alkyl group, alkenylene group or alkynylene group substituted with one or more R a ;
  • each R a is independently selected from hydrogen atom, halogen atom, cyano group, nitro group, and SCN group;
  • each R b is independently selected from R a , pentafluorosulfanyl group, Ci-C 6 -alkyl group, and Ci-C 6 -alkyloxy group
  • Ci-C 6 -alkyl group and Ci-C 6 -alkyloxy group are substituted with R a , and/or
  • each R c is independently selected from R a , Ci-C 4 -alkyl group, C3-C6-cycloalkyl group, and C 2 -acyl group
  • Ci-C 4 -alkyl group and the C3-C6-cycloalkyl are substituted with one or more R a , and/or
  • Ci-C3-alkyloxy group substituted with R a , and/or
  • Ci-C3-alkylthio group substituted with R a a Ci-C3-alkylthio group substituted with R a , and/or
  • Ci-C3-alkylsulfoxy group substituted with R a , and/or
  • Ci-C3-alkylsulfonyl group substituted with R a
  • R 1 is a hydrogen atom or methyl group
  • R 1 is substituted at position 8;
  • R 2 is a phenyl group substituted with up to 3 R b ;
  • R 3 represents R a , a Ci-C 6 -alkyl group
  • Ci-C 4 -alkyloxy group substituted with R a a Ci-C 4 -alkyloxy group substituted with R a , and/or
  • Ci-C 6 -alkylthio group substituted with R a , and/or
  • Ci-C 6 -alkylamino group substituted with R a having 2 substitutent groups inde- pendently selected from hydrogen atom, Ci-C 4 -alkyl group, and C 2 -acyl group), and/or
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom
  • Ci-C3-alkyloxy group substituted with R a , and/or
  • Ci-C3-cycloalkylthio group substituted with R a a Ci-C3-cycloalkylthio group substituted with R a , and/or
  • Ci-C3-alkylsulfoxy group substituted with R a , and/or
  • Ci-C3-alkylsulfonyl group substituted with R a a Ci-C3-alkylsulfonyl group substituted with R a
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom);
  • R 4 is a hydrogen atom, fluorine atom, chlorine atom, cyano group, methyl group, ethyl group, methyloxy group, ethyloxy group, amino group, N-methylamino group, N,N- dimethylamino group, trifluoromethyl group, or nitro group;
  • R 5 is a Ci-C2-alkyl group substituted with one or more R a ;
  • each R a is independently selected from hydrogen atom, halogen atom, cyano group, nitro group, SCN group, and hydroxyl group;
  • each R b is independently selected from hydrogen atom, fluorine atom, chlorine atom, bro- mine atom, iodine atom, pentafluorosulfanyl group, methyl group, ethyl group, n-pro- pyl group, i-propyl group, c-propyl group, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, methyloxy group, ethyloxy group, n-propyloxy group, i- propyloxy group, trifluoromethyloxy group, 2,2,2-trifluoroethyloxy group, methylthio group, methylsulfoxy group, and methylsulfonyl group; and
  • R c is independently selected from hydrogen, methyl group, ethyl group, n-propyl group, i-propyl group, c-propyl group, monofluoromethyl group, difluoromethyl group, trifluo romethyl group, methyloxy group, ethyloxy group, n-propyloxy group, i-propyloxy group, c-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tri fluoromethyloxy group, 2,2,2-trifluoroethyloxy group, methylthio group, methylsulfoxy group, methylsulfonyl group, phenyl group substituted with R a , and pyridyl group substituted with R a .
  • R 1 is a hydrogen atom or methyl group
  • R 2 is a phenyl group substituted with up to 3 R b ;
  • R 3 represents R a , a Ci-C 6 -alkyl group
  • Ci-C 4 -alkyloxy group substituted with R a a Ci-C 4 -alkyloxy group substituted with R a , and/or
  • Ci-C 6 -alkylthio group substituted with R a and/or a Ci-C 6 -alkylamino group substituted with R a (having 2 substitutent groups inde- pendently selected from hydrogen atom, Ci-C4-alkyl group, and C2-acyl group), and/or
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom
  • Ci-C3-alkyl group substituted with R a , and/or
  • Ci-C3-alkyloxy group substituted with R a , and/or
  • Ci-C3-cycloalkylthio group substituted with R a a Ci-C3-cycloalkylthio group substituted with R a , and/or
  • Ci-C3-alkylsulfoxy group substituted with R a , and/or
  • Ci-C3-alkylsulfonyl group substituted with R a a Ci-C3-alkylsulfonyl group substituted with R a
  • heterocyclic group is a structure comprising 2-6 carbon atoms and 1-2 heteroatoms, and the heteroatom(s) is/are independently selected from oxygen atom, nitrogen atom and sulfur atom);
  • R 4 is a hydrogen atom, fluorine atom, chlorine atom, cyano group, methyl group, ethyl group, methyloxy group, ethyloxy group, amino group, N-methylamino group, N,N- dimethylamino group, trifluoromethyl group, or nitro group;
  • R 5 is a Ci-C2-alkyl group substituted with one or more R a ;
  • each R a is independently selected from hydrogen atom, halogen atom, cyano group, nitro group, SCN group, and hydroxyl group;
  • each R b is independently selected from hydrogen atom, fluorine atom, chlorine atom, bro- mine atom, iodine atom, pentafluorosulfanyl group, methyl group, ethyl group, n-pro- pyl group, i-propyl group, c-propyl group, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, methyloxy group, ethyloxy group, n-propyloxy group, i- propyloxy group, trifluoromethyloxy group, 2,2,2-trifluoroethyloxy group, methylthio group, methylsulfoxy group, and methylsulfonyl group; and
  • R c is independently selected from hydrogen, methyl group, ethyl group, n-propyl group, i-propyl group, c-propyl group, monofluoromethyl group, difluoromethyl group, trifluo romethyl group, methyloxy group, ethyloxy group, n-propyloxy group, i-propyloxy group, c-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tri fluoromethyloxy group, 2,2,2-trifluoroethyloxy group, methylthio group, methylsulfoxy group, methylsulfonyl group, phenyl group substituted with R a , and pyridyl group substituted with R a .
  • the method comprises step of contacting the contacting the plant, parts of it, its propagation material, the pests, their food supply, habitat or breeding grounds a pesticidally effective amount of a compound of formula I selected from 1-1 to I-30 from table X,
  • the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all propor- tions as well as isotopic forms such as deuterated compounds.
  • the compounds of formula I may contain one or more asymmetric carbon atoms, and may ex- ist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
  • the compounds according to the invention 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 single pure enantiomers or pure diastereomers of the compounds according to the invention, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds according to the in- vention or their mixtures.
  • Suitable compounds according to the invention also include all possi- ble geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen 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 geomet- rical isomers (cis/trans isomers).
  • the present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
  • the compounds according to the invention may be amorphous or may exist in one or more dif- ferent crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crys- talline states of the respective compounds according to the invention, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds according to the invention are preferably agriculturally and/or veteri- nary acceptable salts, preferably agriculturally acceptable salts. They can be formed in a cus- tomary manner, e.g. by reacting the compound with an acid of the anion in question if the corn- pounds according to the invention have a basic functionality or by reacting acidic compounds according to the invention with a suitable base.
  • Agriculturally useful salts of the compounds according to the invention encompass especially the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the pesticidal action of the compounds according to the invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably Li, Na and K, of the alkaline earth metals, preferably Ca, Mg and Ba, and of the transition metals, preferably Mn, Cu, Zn and Fe, and also ammonium (NH 4 + ) and substituted ammonium in which one to four of the H atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hy- droxyethylammonium, 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-al- kyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, pref- erably formate, acetate, propionate and butyrate. They can be formed by reacting compounds according to the invention 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 ter- tiary nitrogen atom that is oxidized to an N-oxide moiety.
  • genetically modified plant refers to a plant in which the genetic material has been altered in a way that does not occur naturally by mating and/or natural recombination.
  • Examples of genetically modified plants of soybean are YIELD GARD®, Intacta®, lntacta®2, Intacta® Roundup ReadyTM 2 Pro (lntacta®RR2 PRO), Cultivance, Conkesta Soybean, Conkesta Enlist E3TM Soybean, EnlistTM Soybean, Enlist E3TM Soybean, Roundup ReadyTM Soybean, Genuity® Roundup ReadyTM 2 XtendTM, Genuity® Roundup Ready 2 YieldTM, Herbicide-tolerant Soybean line, Optimum GATTM, Liberty LinkTM Soybean, Vistive GoldTM, Verdeca HB4 Soybean,
  • TreusTM, PlenishTM The methods and uses of the invention are for controlling and/or preventing infestation of Faboideae plants, Faboideae crops and Faboideae propagation material by pests.
  • the Faboideae plants, crops or propagation material are soybean plants, crops or propagation material.
  • the pests are from the family of Pentatomidae, family of Agromyzidae, family of Sternorrhyncha, order of Lepidoptera, and/or order of Thysanoptera .
  • the methods and uses of the present invention are applied against pests from the family of Pentatomidae, stink bugs. More preferably against stink bugs that are resistant to other insecticides, e.g. pyre- throid insecticides.
  • Stinkbugs that are "resistant" to a particular insecticide refers e.g. to strains of stinkbugs that are less sensitive to that insecticide compared to the expected sensitivity of the same species of stinkbug. The expected sensitivity can be measured using e.g. a strain that has not previously been exposed to the insecticide.
  • the method comprises applying to Faboideae plants, crops and/or propagation material, in particular soybean plants, soybean crops and/or propagation material of soybean plants, a compound of the invention, wherein the method is for controlling and/or preventing infestation by pests.
  • the method is for controlling and/or preventing infestation by pests from family of Pentatomidae, family of Agromyzidae, family of Sternorrhyncha, order of Lepidoptera, and/or order of Thysanoptera, in particular from the family of Pentatomidae, stink bugs; even more par- ticular for controlling and/or preventing infestation by Acrosternum spp., Euschistus spp.,
  • Nezara spp. Dichelops spp., Edessa spp., Halyomorpha spp., and/or Piezodrus spp., most par- ticularly by Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops furcatus, Edessa meditabunda, Halyomorpha halys, and/or Piezodrus guildini, and especially by Euschistus heros.
  • the method is for controlling and/or preventing infestation by pests from the family of Pentatomidae, Noctuidae, Pyralidae, Agromyzidae, and/or Thripidae (such as Dichromothrips like Dichromothrips corbetti), in particular from the family of Pentatomidae, stink bugs; even more particular for controlling and/or preventing infestation by Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Halyomorpha spp., and/or Piezodrus spp., most particularly by Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops furcatus, Edessa meditabunda, Halyomorpha halys, and/or Piezodrus guildini, and especially by Euschis- tus her
  • a further aspect the invention provides the use of the compounds of the invention for the gen- eral control of pests from the family of Pentatomidae, family of Agromyzidae, family of Sternor- rhyncha, order of Lepidoptera, and/or order of Thysanoptera, preferably for the control of pests from the family of Pentatomidae, in particular for the control of Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Halyomorpha spp. and/or Piezodrus spp., most particularly by Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops furcatus,
  • a further aspect the invention provides the use of the compounds of the invention for the gen- eral control of pests from the family of Pentatomidae (stink bugs), Noctuidae, Pyralidae, Agromyzidae, and/or Thripidae, preferably for the control of pests from the family of Pentatomi- dae, in particular for the control of Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Halyomorpha spp.
  • Piezodrus spp. most particularly by Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops furcatus, Edessa meditabunda, Halyomor- pha halys, and/or Piezodrus guildini, and most preferably for the control of Euschistus heros.
  • the invention provides the use of the compounds of the invention for con- trolling pests that are resistant to one or more other insecticides, preferably pyrethroids, neon- icotinoids and organophosphates, and more preferably pyrethroid insecticides.
  • insecticides preferably pyrethroids, neon- icotinoids and organophosphates, and more preferably pyrethroid insecticides.
  • the compounds of the invention are used for controlling pests from the family of Pentatomidae, stinkbugs, that are resistant to one or more other insecticides, preferably to pyre- throids, neonicotinoids and organophosphates, and more preferably to pyrethroid insecticides, in particular for the control of Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Halyomorpha spp.
  • Euschistus heros most particularly by Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops furcatus, Edessa meditabunda, Halyomorpha halys and/or Piezodrus guildini, and most preferably for the control of Euschistus heros that are resistant to one or more other insecticides, preferably pyrethroids, neonicotinoids and organo- phosphates, and more preferably pyrethroid insecticides.
  • insecticides preferably pyrethroids, neonicotinoids and organo- phosphates, and more preferably pyrethroid insecticides.
  • the compounds applied in the methods or uses of the in- vention may be used on Faboideae, in particular soybean, to control, any of: Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Halyomorpha spp., and/or Piezo- drus spp., most particularly by Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops furcatus, Edessa meditabunda, Halyomorpha halys, and/or Piezodrus guildini, and especially by Euschistus heros;
  • the compounds applied in the methods or uses of the invention may be used on Faboideae, in particular soybean, to control, any of: Agrotis spp., An- ticarsia spp., Chrysodeixis spp., Earias spp., Helicoverpa spp., Heliothis spp., and/or Spodop- tera spp., more particularly by Agrotis ipsilon, Anticarsia gemmatalis, Chrysodeixis includens, Elasmopalpus lignosellus, Helicoverpa armigera, Heliothis virescens, Spodoptera cosmoides, Spodoptera eridania, and/or Spodoptera frugiperda;
  • the compounds applied in the methods or uses of the invention may be used on Faboideae, in particular soybean, to control, any of: Melanagromyza spp., in perticular Melanagromyza soaje.
  • the compounds applied in the methods or uses of the invention may be used on Faboideae, in particular soybean, to control, any of: Dichromothrips ssp., and/or Caliothrips spp., most particularly by Dichromothrips corbetti, and/or Caliothrips brasiliensis;
  • the compounds applied in the methods or uses of the invention may be used on Faboideae, in particular soybean, to control, any of: Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Halyomorpha spp., Piezodrus spp., Agrotis spp., Anticarsia spp., Chrysodeixis spp., Earias spp., Helicoverpa spp., Heliothis spp., Spodoptera spp., Dichromothrips ssp., Melanagromyza spp., and/or Caliothrips spp.;
  • the compounds applied in the methods or uses of the invention may be used on Faboideae, in particular soybean, to control, any of: Acrosternum hilare, Euschistus her
  • the compounds applied in the methods of the invention may be used on Faboideae, in partic- ular soybean, to control, any of: Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Halyomorpha spp., Piezodrus spp., Agrotis spp., Anticarsia spp., Chryso- deixis spp., Earias spp., Helicoverpa spp., Heliothis spp., Spodoptera spp., Dichromothrips ssp., Melanagromyza spp., and/or Caliothrips spp., preferably Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops furcatus, Edessa meditabunda, Halyomorpha halys, Pi
  • the compounds of the invention are preferably used on Faboideae, in particular soybean, to control stinkbugs, e.g. Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilaris), Pie- zodorus spp. (e.g. Piezodorus guildinii), Acrosternum spp. (e.g. Acrosternum hilare), Euschistus spp. (e.g. Euschistus heros, Euschistus servus), Edessa spp. (e.g. Edessa meditabunda), Halyomorpha halys, Dichelops spp. (e.g.
  • Bemisia spp. e.g. Bemisia tabaci, Bemisia argentifolii
  • Preferred targets include Acrosternum hilare, Euschistus heros, Nezara viridula, Dichelops fur- catus, Edessa meditabunda, Halyomorpha halys, Piezodrus guildini, Agrotis ipsilon, Anticarsia gemmatalis, Chrysodeixis includens, Elasmopalpus lignosellus, Helicoverpa armigera, Heliothis virescens, Spodoptera cosmoides, Spodoptera eridania, Spodoptera frugiperda, Dichromothrips corbetti, Melanagromyza soaje, and/or Caliothrips brasiliensis.
  • the stinkbug target is Nezara viridula, Piezodorus spp., Acrosternum spp., Euschistus heros. Euschistus and in particular Euschistus heros are the preferred targets.
  • the pests are from the family of Pentatomidae, fam- ily of Agromyzidae, family of Sternorrhyncha, order of Lepidoptera, and/or order of Thysanop- tera, more preferably from the family of Pentatomidae, Agromyzidae, order of Lepidoptera, and/or order of Thysanoptera.
  • the pests are from the family of Pentatomidae, Agromyzidae, Noctuidae, Pyralidae, and/or Thripidae, more preferably from the family of Penta- tomidae, Agromyzidae, Noctuidae, and/or Thripidae.
  • the pests are selected from Acrosternum spp., Euschistus spp., Nezara spp., Dichelops spp., Edessa spp., Edessa meditabunda, Eu- schistus heros, Euschistus impictiventris, Euschistus variolarius, Euschistus servus, Nezara viridula, Piezodorus guildinii, Halyomorpha halys, Euschistus servus, Euschistus variolarius, Halyomorpha halys, Dichromothrips corbetti, Caliothrips brasiliensis, Agrotis ipsilon, Anticarsia gemmatalis, Chrysodeixis includens, Helicoverpa armigera, Heliothis virescens, Spodoptera cosmoides, Spodoptera eridania, Melanagromyza soaje, and/
  • the pests are Acrosternum hilare, Euschistus heros, Nezara viridula, and/or Piezodorus guildini.
  • the pests are Heliothis virescens, Halyomor- pha halys, Spodoptera eridania, Bemisia argentifolii, Dichromothrips corbetti, Euschistus heros, and/or Nezara viridula.
  • Further pests that can be controlled according to the invention are from the family of Sternor- rhyncha, in particular Bemisia spp., more particularly Bemisia tabaci and/or Bemisia argentifolii.
  • the invention relates to methods and uses, wherein the compound of the formula (I) is applied in an application type which corresponds in each case to one row of Table A.
  • the invention relates to methods and uses, wherein the compound of the formula (I) as component I and at least one mixing partner as defined below, are applied in an application type which corresponds in each case to one row of Table A.
  • Application of the compounds of the invention is preferably to a crop of Faboideae, such as soybean; the locus thereof or propagation material thereof.
  • Preferably application is to a crop of Faboideae, such as soybean or the locus thereof, more preferably to a crop of soybean plants.
  • Application may be before infestation or when the pest is present.
  • Application of the compounds of the invention can be performed according to any of the usual modes of application, e.g. foliar, drench, soil, in furrow etc. Control of stinkbugs can be achieved by foliar application, which is a preferred mode of application according to the invention.
  • the compounds of the invention are applied to Faboideae crops by soil-drench application.
  • the Faboideae crops are soybean crops.
  • the compounds of the invention are applied as seed- treatment to seeds of Faboideae, and Bt Faboideae crops.
  • the Faboideae crops are soybean crops, particularly Bt soybean crops.
  • the pest e.g. the stink bugs, the plant, soil or water in which the plant is growing can be con- tacted with the compounds of the invention or composition(s) containing them by any further ap- plication method known in the art.
  • "contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest or plant).
  • the compounds of the invention or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially from stink bugs, in particular from Euschistus, more particularly from E. heros, by contacting the plant/crop with a pesticidally effective amount of compounds of the invention.
  • crop refers both to growing and harvested crops.
  • the compounds of the invention may be applied in combination with an attractant.
  • An attract- ant is a chemical that causes the insect to migrate towards the location of application.
  • an attract- ant for con- trol of stinkbugs it can be advantageous to apply the compounds of the invention with an attract- ant, particularly when the application is foliar. Stinkbugs are often located near to the ground, and application of an attractant may encourage migration up the plant towards the active ingre- dominant.
  • Suitable attractants include glucose, sacchrose, salt, glutamate, citric acid, soybean oil, peanut oil and soybean milk. Glutamate and citric acid are of particular interest, with citric acid being preferred.
  • An attractant may be premixed with the compound of the invention prior to application, e.g. as a readymix or tankmix, or by simultaneous application or sequential application to the plant. Suitable rates of attractants are for example 0.02 kg/ha-3 kg/ha.
  • the compounds of the invention are preferably used for pest control on Faboideae, in particu- lar soybean, at 1-500 g/ha, preferably 10-100 g/ha.
  • the compounds of the invention are suitable for use on any Faboideae plant, such as soybean plants, including those that have been genetically modified to be resistant to active ingredients such as herbicides or to produce biologically active compounds that control infestation by plant pests.
  • transgenic plants and plant cultivars obtained by genetic engineering methods are treated.
  • plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.
  • Plant cultivars are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques.
  • the preferred transgenic plants or plant cultivars which are to be treated according to the invention include all plants which, by virtue of the genetic modifi- cation, received genetic material which imparts particularly advantageous, useful traits to these plants.
  • Examples of such traits are better plant growth, increased tolerance to high or low tempera- tures, increased tolerance to drought or to water or soil salt content, increased flowering perfor- mance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.
  • Bt plants Cry1 C, Cry2A, Cry3A, Cry3B2, Cry9c, Cry2Ab, Cry2Ab2, Cry3Bb, Cry3Bb1 , Cry34Ab1 , Cry35Ab1 , Cry3A, mCry3A and Cry1 F, Cry1 Fa2, dvsnf7, moCryl F, pinll, vip3Aa and vip3Aa20 and also combinations thereof) (referred to herein as "Bt plants”). Traits that are also particularly emphasized are the increased defense of the plants against fungi, bacteria and viruses by sys- temic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR sys- temic acquired resistance
  • trasits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene).
  • herbicidally active compounds for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene).
  • PAT phosphinotricin
  • Bt plants are soybean varieties which are sold under the trade names YIELD GARD®, Intacta®, lntacta®2, Intacta® Roundup ReadyTM 2 Pro (lntacta®RR2 PRO), Cul- tivance, Conkesta Soybean, Conkesta Enlist E3TM Soybean, EnlistTM Soybean, Enlist E3TM Soy- bean, Roundup ReadyTM Soybean, Genuity® Roundup ReadyTM 2 XtendTM, Genuity®
  • Roundup Ready 2 YieldTM Herbicide-tolerant Soybean line, Optimum GATTM, Liberty LinkTM Soybean, Vistive GoldTM, Verdeca HB4 Soybean, TreusTM, PlenishTM.
  • herbicide-tolerant plants which may be mentioned are soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate), Liberty Link® (tol erance to phosphinotricin), I Ml® (tolerance to imidazolinones) and STS® (tolerance to sulpho- nylureas).
  • Roundup Ready® tolerance to glyphosate
  • Liberty Link® tol erance to phosphinotricin
  • I Ml® tolerance to imidazolinones
  • STS® tolerance to sulpho- nylureas
  • An example of a glyphosate tolerant soybean cultivar is BMX Potencia.
  • Herbicide-resistant plants plants bred in a conventional manner for herbicide tolerance
  • plants bred in a conventional manner for herbicide tolerance include the varieties sold under the name Clearfield® (for example maize).
  • the compounds of the invention are applied to Faboideae, in particular soybean plants, carrying two or more traits (e.g. Enlist®), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba (Monsanto) HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer Crop- Science, Syngenta). Double or triple stack in soybean plants of any of the traits described here are also of interest, including glyphosate and sulfonyl -urea tolerance (e.g.
  • the present invention also relates to a method for controlling pests and/or increasing the plant health of a cultivated plant as compared to the respective non-modified control plant, comprising the application of the compound of the formula (I), to a plant with at least one modification, parts of such plant, plant propagation material, or at its locus of growth, wherein the cultivated plant is (i) Glycine max L.
  • present invention also relates to a method for controlling pests and/or increasing the plant health of a cultivated plant as compared to the respective non-modified control plant, corn- prising the application of the compound of the formula (I), to a plant with at least one modifica- tion, parts of such plant, plant propagation material, or at its locus of growth, wherein the culti vated plant is modified by at least one gene according to one row of table D.
  • the present invention also relates to a mixture of at least one compound of the present inven- tion with at least one mixing partner as defined herein after.
  • Preferred are binary mixtures of one compound of the present invention as component I with one mixing partner as defined herein after as component II.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly pref- erably from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • GABA-gated chloride channel antagonists such as: fiproles (phenylpyrazoles): ethiprole, fipronil, or pyriprole;
  • Sodium channel modulators from the class of pyrethroids bifenthrin, lambda-cyhalothrin, alpha-cypermethrin or deltamethrin;
  • Nicotinic acetylcholine receptor agonists from the class of neonicotinoids: clothi- anidin, dinotefuran, imidacloprid, thiacloprid, or thiamethoxam;
  • Chloride channel activators from the class of avermectins and milbemycins abamectin, emamectin benzoate, or ivermectin;
  • Inhibitors of the chitin biosynthesis type 1 buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines: tebufenozide;
  • M.15 insecticidal active compounds of unknown or uncertain mode of action: afidopyropen, broflanilide, flupyradifurone, or sulfoxaflor;
  • the M.3 neonicotinoid cycloxaprid is known from WO2010/069266 and WO201 1/069456, the neonicotinoid M.3, sometimes also to be named as guadipyr, is known from WO2013/003977, and the neonicotinoid M.3 (approved as paichongding in China) is known from
  • the metaflumizone analogue M.12 is described in CN10171577 and the ana- logue in CN102126994.
  • the phthalamides M.14 are known from W02007/101540.
  • the an- thranilamide M.14 is described in W02005/077934.
  • the broflanilide are described in
  • the mixing partner is selected from ethiprole, fipronil or pyriprole from group M.1 ; lambda cyhalothrin, alpha-cypermethrin, bifenthrin or deltamethrin from group M.2; dinotefuran, clothianidin, thiacloprid, imidacloprid or thiamethoxam from group M.3; spi- nosad from group M.4; ivermectin, abamectin, avermectin or emamectin from group M.5; floni- camid, pymetrozine from group M.6; chlorfenapyr from group M.7; teflubenzuron from group M.8; buprofezin from group M.9; tebufenozide from group M.10; amitraz from group M.1 1 ; meta- flumizone from group M.12;
  • the mixing partner is selected from pyrethroids for example lambda cyhalothrin, alpha-cypermethrin, bifenthrin and deltamethrin from group M.2; or neon- icotinoids for example dinotefuran, clothianidin, thiacloprid, imidacloprid or thiamethoxam from group M.3.
  • pyrethroids for example lambda cyhalothrin, alpha-cypermethrin, bifenthrin and deltamethrin from group M.2
  • neon- icotinoids for example dinotefuran, clothianidin, thiacloprid, imidacloprid or thiamethoxam from group M.3.
  • the mixing partner is particularly selected from pyre- throids for example lambda cyhalothrin, alpha-cypermethrin, bifenthrin and deltamethrin from group M.2.
  • Insecticidal compositions for use typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.
  • Ready-to-use preparations contain the compounds acting against parasites, preferably ecto- parasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
  • Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
  • the compounds of the invention may be applied in the methods of the present invention in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers).
  • Suitable formulation types include granules of fertilizer.
  • the mixtures preferably contain up to 25 % by weight of the compound of the invention.
  • An additional mixing partner may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for exam- pie by increasing the speed of effect or overcoming repellency) of the compound of the inven- tion; or help to overcome or prevent the development of resistance to individual components.
  • the particular additional active ingredient will depend upon the intended utility of the composi- tion.
  • the compounds of the invention may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
  • synergists for use in the compositions include piperonyl butoxide, sesa- mex, safroxan, and dodecyl imidazole.
  • Preferred methods and uses of the invention applying the compound of formula I to a plant se- lected from RR Soybean, Intacta® Soybean, lntacta®2 Soybean, and Intacta® RR2 PRO Soy- bean, Conkesta Soybean, Conkesta Enlist E3TM Soybean, and, particularly to Intacta® soybean, lntacta®2, and Intacta® RR2 PRO.
  • Particularly preferred methods are directed to applying the compound of formula I to plants and pests are given in Table 1-1 to Table 1-32.
  • Table 1-1 Methods and uses, wherein the compound of formula 1.1 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1-2 Methods and uses, wherein the compound of formula 1.2 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1-3 Methods and uses, wherein the compound of formula 1.3 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1-7 Methods and uses, wherein the compound of formula 1.7 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1-8 Methods and uses, wherein the compound of formula 1.8 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1-9 Methods and uses, wherein the compound of formula 1.9 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1 -10 Methods and uses, wherein the compound of formula 1.10 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -1 1 Methods and uses, wherein the compound of formula 1.1 1 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -12 Methods and uses, wherein the compound of formula 1.12 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -13 Methods and uses, wherein the compound of formula 1.13 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -14 Methods and uses, wherein the compound of formula 1.14 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -15 Methods and uses, wherein the compound of formula 1.15 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -16 Methods and uses, wherein the compound of formula 1.16 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1 -17 Methods and uses, wherein the compound of formula 1.17 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -18 Methods and uses, wherein the compound of formula 1.18 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • Table 1 -20 Methods and uses, wherein the compound of formula 1.20 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -21 Methods and uses, wherein the compound of formula 1.21 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -22 Methods and uses, wherein the compound of formula 1.22 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -24 Methods and uses, wherein the compound of formula 1.24 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1 -30 Methods and uses, wherein the compound of formula 1.30 is applied to plant and/or pests which corresponds in each case to one row of T able T.
  • Table 1-31 Methods and uses, wherein the compound of formula 1.31 is applied to plant and/or pests which corresponds in each case to one row of Table T.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
  • An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof.
  • the term "pesticidally effective amount” is defined below.
  • compositions e.g. solutions, emulsions, suspensions, dusts, pow- ders, 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.
  • compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Mono- graph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac- tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec- tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu- lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi- ers and binders.
  • suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac- tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec- tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu- lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac- tions 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, al- kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil frac- tions 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, tetrahydrona
  • 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, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammo- nium 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, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.
  • 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 col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De- tergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul- fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl-sul- fonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sul- fonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sul- fates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox-ylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Exam-pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth-oxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • Exam- pies of 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 alkylpoly- glucosides.
  • polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vi- nylalcohols, 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 pol- ymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene ox ide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suita- ble polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers.
  • polybases are polyvinylamines or polyeth- yleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present in- vention 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), anor- ganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • 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. polyvi- nylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
  • dispersant e. g. polyvi- nylpyrrolidone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insol- uble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium do- decylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble or- ganic solvent e.g. aromatic hydrocarbon
  • 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 alco- hol 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 sub- stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
  • WG, SG Water-dispersible granules and water-soluble granules
  • 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 solu- tion 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 ad- dition 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 dis persion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 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 sub- stance. 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. alko- hol ethoxylate and arylphenol ethoxylate), and water up to 100 %.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alko- hol 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. methyl- methacrylate, 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 radi-cal initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase compris- ing 5-50 wt% of a compound I according to the invention, 0-40 wt% water insolu-ble organic sol- vent (e.g.
  • an isocyanate monomer e.g. diphenylme-thene-4,4’- diisocyanatae
  • a protective colloid e.g. polyvinyl alco- hol
  • the addition of a polyamine results in the for-mation of a pol- yurea microcapsule.
  • the monomers amount to 1-10 wt%. The wt% relate to the total CS corn- position.
  • 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.
  • 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
  • 1-50 wt% of 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 xi) 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% col- ora nts.
  • 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% col- ora nts.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably be- tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immedi- ately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochem- ical composition is made up with water, buffer, and/or further auxiliaries to the desired applica- tion concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the in- vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the in- vention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the in- vention or partially premixed components e. g. components comprising compounds of the pre- sent invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
  • the compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from at- tack or infestation by animal pests. Therefore, the present invention also relates to a plant pro- tection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infesta- tion by animal pests, with a pesticidally effective amount of a compound of the present inven- tion.
  • the compounds of the present invention are also suitable for use in combating or controlling animal pests.
  • the present invention also relates to a method of combating or control- ling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesti- cidally effective amount of a compound of the present invention.
  • the compounds of the present invention are effective through both contact and ingestion.
  • Fur- thermore the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions compris- ing said mixtures as defined above.
  • the components of said mixture can be applied simultane- ously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture“in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow appli cation, and foliar application.
  • Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
  • Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pellet ing.
  • furrow applications typically include the steps of making a furrow in cultivated land, seed- ing the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.
  • the term "contacting” includes both direct contact (applying the compounds or compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
  • crop refers to both, growing and harvested crops.
  • plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • iceberg lettuce chic- ory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g.
  • Preferred plants include potatoes sugar beets, to- bacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant is to be understood as including plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
  • Plants which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular soybean.
  • rapeseed e.g. oilseed rape
  • bean carnation
  • chicory cotton
  • eggplant eucalyptus
  • flax flax
  • lentil lentil
  • melon melon
  • papaya petunia
  • plum poplar
  • potato rice
  • soybean zucchini
  • squash sugar beet
  • sugarcane sugarcane
  • sunflower sweet pepper
  • sweet pepper tobacco, tomato, and cereals
  • the one or more mutagenized or integrated genes are preferably se- lected from pat, epsps, Cry1A, CrylAb, CrylAb(truncated), Cry1Ab-Ac, CrylAc, Cry1A.105, Cry1 C, Cry2A, Cry3A, Cry3B2, Cry9c, Cry2Ab, Cry2Ab2, Cry3Bb, Cry3Bb1 , Cry34Ab1 , Cry35Ab1 , Cry3A, mCry3A and Cry1 F, Cry1 Fa2, dvsnf7, moCryl F, pinll, vip3Aa and vip3Aa20, dfr, barnase, barstar, als, bxn, bp40, asn1 , and ppo5.
  • the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant.
  • properties also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control.
  • herbicide tolerance e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance
  • Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield® oilseed rape being tolerant to imidazoli- nones, e.g. imazamox.
  • genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • glyphosate and glufosinate some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • herbicides such as glyphosate and glufosinate
  • RoundupReady® glyphosate
  • LibertyLink® glufosinate
  • insect resistance is of importance, in particular lepidopteran insect resistance.
  • Insect resistance is typically achieved by
  • Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singu- lar traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the com- bination of herbicide tolerance and insect resistance, are of increasing importance.
  • the pesticidal activity of the compounds of the invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become re- sistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a com- plementary insecticidal activity can advantageously be used.
  • plant propagation material refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhi- zomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • vegetative plant material such as cuttings and tubers (e.g. potatoes)
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/composi- tions used in the invention.
  • a pesticidally effective amount of the compositions will also vary ac- cording to the prevailing conditions such as desired pesticidal effect and duration, weather, tar- get species, locus, mode of application, and the like.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • the rate of application of the active in- gredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hec- tare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the present invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects.
  • the present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermina- tion with a compound of the present invention.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking in- sects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
  • seed treatment application of the active compound is car- ried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the present invention also comprises seeds coated with or containing the active compound.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
  • Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, orna- mentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, ba- nanas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucum- bers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include for example flowable concentrates FS, solu- tions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the lat- ter. Preferably, the formulations are applied such that germination is not included.
  • the active substance concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
  • a FS formulation is used for seed treatment.
  • a FS formu- lation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially preferred FS formulations of the compounds of the present invention for seed treat- ment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
  • a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein.
  • the amount of the compound of the pre- sent invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • the active compound is dissolved at the desired concentration in a mixture of 1 :1 (vokvol) dis tilled water : acetone.
  • Surfactant Kinetic® HV
  • the test so- lution is prepared at the day of use.
  • Soybean pods were placed in 90 x 50 mm glass Petri dishes lined with moist filter paper and inoculated with ten late 3rd instar N. viridula. Using a hand atomizer, an approximately 2 ml so- lution is sprayed into each Petri dish. Treated cups were kept at about 25-26°C and relative hu- midity of about 65-70%. Percent mortality was recorded after 5 days.
  • test unit For evaluating control of Euschistus heros through contact the test unit consisted of 100 ml disposable plastic beakers with transparent lids.
  • the compounds or mixtures of compounds were formulated using a solution containing 50% water and 50% acetone. 50 ml of different concentrations of formulated compounds or mixtures were prepared in a glass petri dish and used for dipping three 6 cm sections of fresh pole bean. Each treatment was replicated eight times.
  • pole bean sections were air-dried and 5 adult E. heros placed in each beaker.
  • the E. heros were then allowed to suck on the treated pole bean sections and incu- bated at 23 + 1 °C, 50 + 5 % RH for 5 days. E. heros mortality was then visually assessed.
  • Halyomorpha halys (Brown Marmorated Stink Bug)
  • the active compound is dissolved at the desired concentration in a mixture of 1 :1 (vokvol) distilled water : acetone with 0.005% (v/v) of Tween 20 added as surfactant.
  • Soybean seeds are placed in a small petri dish inside a plastic cup 10 adults (5 females and 5 males) are introduced into each cup.
  • adults (5 females and 5 males) are introduced into each cup.
  • Using an airbrush sprayer 1 mL solution was sprayed directly inside the cups with bean pods. After drying, a water source (wet cotton in a small petri dish) is placed in each cup, and the cups closed with ventilated cover. All cups held under constant temperature of 20°C, 16L8D photoperiod. Live insects are counted at 5 days after treatment.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un procédé de lutte contre des nuisibles des plants de soja, comprenant l'étape consistant à mettre en contact le plant de soja, des parties de celui-ci, son matériau de propagation, les nuisibles, leur approvisionnement en nourriture, leur habitat ou leurs lieux de reproduction avec au moins un composé de formule (I), dans laquelle les variables sont définies tel qu'indiqué dans la description et les revendications.
PCT/EP2019/060141 2018-04-30 2019-04-18 Lutte contre des nuisibles des plants de soja avec des composés méso-ioniques WO2019211106A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN201821016237 2018-04-30
IN201821016237 2018-04-30

Publications (1)

Publication Number Publication Date
WO2019211106A1 true WO2019211106A1 (fr) 2019-11-07

Family

ID=66397205

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2019/060141 WO2019211106A1 (fr) 2018-04-30 2019-04-18 Lutte contre des nuisibles des plants de soja avec des composés méso-ioniques

Country Status (1)

Country Link
WO (1) WO2019211106A1 (fr)

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005077934A1 (fr) 2004-02-18 2005-08-25 Ishihara Sangyo Kaisha, Ltd. Anthranilamides, procédé pour la production de ceux-ci et agents antiparasitaires contenant ceux-ci
WO2007101540A1 (fr) 2006-03-06 2007-09-13 Bayer Cropscience Ag Combinaisons de principes actifs à propriétés insecticides
WO2007101369A1 (fr) 2006-03-09 2007-09-13 East China University Of Science And Technology Méthode de préparation et utilisation de composés présentant une action biocide
WO2010018714A1 (fr) 2008-08-13 2010-02-18 三井化学アグロ株式会社 Dérivé amide, agent antiparasitaire contenant le dérivé amide et utilisation de l’agent antiparasitaire
WO2010069266A1 (fr) 2008-12-19 2010-06-24 华东理工大学 Composés azotés ou oxygénés hétérocycliques ayant une activité insecticide formés à partir de dialdéhydes et leur préparation et leurs utilisations
WO2011017334A2 (fr) * 2009-08-05 2011-02-10 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
WO2011069456A1 (fr) 2009-12-09 2011-06-16 华东理工大学 Composés néonicotinoïdiques hétérocycliques bivalents et oxapontés et leurs procédés de préparation
CN102126994A (zh) 2010-01-19 2011-07-20 中化蓝天集团有限公司 一种二苯酮腙衍生物、其制备方法和用途
WO2013003977A1 (fr) 2011-07-01 2013-01-10 合肥星宇化学有限责任公司 Composé de 3-nitroimino-1,2,4-triazoline 2,5-disubstituée et son procédé de préparation et son utilisation comme pesticide
WO2016171053A1 (fr) 2015-04-21 2016-10-27 日本化薬株式会社 Composé mésoionique
WO2017140614A1 (fr) * 2016-02-19 2017-08-24 Basf Se Procédé de lutte contre des parasites de plants de soja, de maïs et de coton
WO2018062082A1 (fr) 2016-09-28 2018-04-05 日本化薬株式会社 Nouveau composé insecticide mésoionique

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005077934A1 (fr) 2004-02-18 2005-08-25 Ishihara Sangyo Kaisha, Ltd. Anthranilamides, procédé pour la production de ceux-ci et agents antiparasitaires contenant ceux-ci
WO2007101540A1 (fr) 2006-03-06 2007-09-13 Bayer Cropscience Ag Combinaisons de principes actifs à propriétés insecticides
WO2007101369A1 (fr) 2006-03-09 2007-09-13 East China University Of Science And Technology Méthode de préparation et utilisation de composés présentant une action biocide
WO2010018714A1 (fr) 2008-08-13 2010-02-18 三井化学アグロ株式会社 Dérivé amide, agent antiparasitaire contenant le dérivé amide et utilisation de l’agent antiparasitaire
WO2010069266A1 (fr) 2008-12-19 2010-06-24 华东理工大学 Composés azotés ou oxygénés hétérocycliques ayant une activité insecticide formés à partir de dialdéhydes et leur préparation et leurs utilisations
WO2011017334A2 (fr) * 2009-08-05 2011-02-10 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
WO2011069456A1 (fr) 2009-12-09 2011-06-16 华东理工大学 Composés néonicotinoïdiques hétérocycliques bivalents et oxapontés et leurs procédés de préparation
CN102126994A (zh) 2010-01-19 2011-07-20 中化蓝天集团有限公司 一种二苯酮腙衍生物、其制备方法和用途
WO2013003977A1 (fr) 2011-07-01 2013-01-10 合肥星宇化学有限责任公司 Composé de 3-nitroimino-1,2,4-triazoline 2,5-disubstituée et son procédé de préparation et son utilisation comme pesticide
WO2016171053A1 (fr) 2015-04-21 2016-10-27 日本化薬株式会社 Composé mésoionique
WO2017140614A1 (fr) * 2016-02-19 2017-08-24 Basf Se Procédé de lutte contre des parasites de plants de soja, de maïs et de coton
WO2018062082A1 (fr) 2016-09-28 2018-04-05 日本化薬株式会社 Nouveau composé insecticide mésoionique
AU2017335450A1 (en) * 2016-09-28 2019-04-11 Nippon Kayaku Kabushiki Kaisha Novel mesoionic insecticidal compound

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
HENKEL, J.: "Soy: Health Claims for Soy Protein, Question About Other Components", FDA CONSUMER (FOOD AND DRUG ADMINISTRATION, vol. 34, no. 3, 2000, pages 18 - 20
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
KNOWLES: "Agrow Reports DS256", 2006, T&F INFORMA, article "Adjuvants and additives"
MCCUTCHEON'S: "Emulsifiers & Detergents", vol. 1, 2008, MCCUTCHEON'S DIRECTORIES
MOLLET; GRUBE-MANN: "Formulation technology", 2001, WILEY VCH

Similar Documents

Publication Publication Date Title
AU2018241628B2 (en) Pyrimidinium compounds and their mixtures for combating animal pests
US11021413B2 (en) Benzylpropargylether as nitrification inhibitors
UA123912C2 (uk) Біциклічні сполуки
SE517612C2 (sv) Användning av 5-amino-4-etylsulfinyl-1-arylpyrazol föreningar som pesticider
JP2012506891A (ja) 植物の健康を改善する方法
JP2012506892A (ja) 植物の健康を改善する方法
WO2017140614A1 (fr) Procédé de lutte contre des parasites de plants de soja, de maïs et de coton
UA125047C2 (uk) Біциклічні пестицидні сполуки
US10165778B2 (en) Method for controlling pests in soybean
CA3011604A1 (fr) Melanges a activite pesticide comprenant des composes anthranilamides
US9549552B2 (en) Active compound combinations having insecticidal properties
WO2019185413A1 (fr) Dérivés de cyclopropyle substitués pesticides
WO2019121143A1 (fr) Dérivés de cyclopropyle substitués
WO2019134840A1 (fr) Lutte contre les ravageurs de plants de soja avec des composés méso-ioniques
WO2019211106A1 (fr) Lutte contre des nuisibles des plants de soja avec des composés méso-ioniques
TWI804514B (zh) 用於對抗動物有害生物之嘧啶鎓化合物及其混合物
US20220039386A1 (en) Method for controlling pests of rapeseed plants
KR20150144777A (ko) 프탈디이미드 유도체와 아바멕틴, 에마멕틴, 레피멕틴 또는 밀베멕틴의 살충성 상승적 배합물
RU2809600C2 (ru) Способ борьбы с вредителями растений картофеля
RU2827556C9 (ru) Способ борьбы с вредителями растений рапса
RU2827556C2 (ru) Способ борьбы с вредителями растений рапса
NZ731389B2 (en) Benzylpropargylether as nitrification inhibitors

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19721557

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19721557

Country of ref document: EP

Kind code of ref document: A1