WO2013190050A1 - Procédés de lutte contre des insectes - Google Patents

Procédés de lutte contre des insectes Download PDF

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Publication number
WO2013190050A1
WO2013190050A1 PCT/EP2013/062901 EP2013062901W WO2013190050A1 WO 2013190050 A1 WO2013190050 A1 WO 2013190050A1 EP 2013062901 W EP2013062901 W EP 2013062901W WO 2013190050 A1 WO2013190050 A1 WO 2013190050A1
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Prior art keywords
phenyl
cycle
anthonomus
trifluoromethyl
chloro
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PCT/EP2013/062901
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English (en)
Inventor
Myriem El Qacemi
Jérôme Yves CASSAYRE
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Syngenta Participations Ag
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Publication of WO2013190050A1 publication Critical patent/WO2013190050A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to a method of controlling insects, in particular insects of the family Curculionidae, and in particular in cotton.
  • Insects of the Curculionidae family are almost entirely plant feeders.
  • Several members of this family in particular members of the genus Anthonomus, are known to be important agronomic pests in a variety of commercially important flowering crops and flowering ornamental plants.
  • Weevils are known to attack, inter alia, cotton, apple, hazelnut, oil seed rape, strawberry and pepper crops.
  • Curculionidae in particular Anthonomus, suffer several disadvantages.
  • One of these, endosulfan, has been banned in over 80 countries due to its threat to human health and the environment.
  • Pyrethroids such as cyfluthrin and betacyfluthrin are less effective now due to the appearance of resistance.
  • insecticides which can be used to control Curculionidae, in particular Anthonomus.
  • GABA gamma-aminobutyric acid
  • GABA gamma- aminobutyric acid
  • the compounds of interest include a thietane amide derivative in which the thietane carbon ring members are unsubstituted.
  • the invention provides a method comprising applying to a crop of cotton plants, the locus thereof, or propagation material thereof, a compound of formula I wherein
  • cycle A is Ala or A2a
  • a 1 , A 2 , A 3 and A 4 are independently C-H, or nitrogen and wherein #1 indicates the bond to X and #2 indicates the bond to cycle B;
  • cycle B is selected from Bl to B6
  • #1 indicates the bond to cycle A
  • #2 indicates the bond to R 7
  • #3 indicates the bond to cycle C
  • cycle C is phenyl
  • R 5 is chloro, bromo, CF 3 or methyl
  • R 7 is chlorodifluoromethyl or trifluoromethyl
  • each R 8 is independently bromo, chloro, fluoro or trifluoromethyl
  • p 1, 2 or 3;
  • X is selected from PI to P9
  • the invention provides a method of controlling and/or preventing infestation of insects of the family Curculionidae in cotton comprising applying to a crop of cotton plants, the locus thereof, or propagation material thereof, a compound that of formula I.
  • the insects of the family are of the family Curculionidae in cotton.
  • Curculionidae may be those that are resistant to one or more other insecticides.
  • the invention provides a method of controlling and/or preventing infestation of insects of the family Curculionidae in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I.
  • the insects of the family Curculionidae may be those that are resistant to one or more other insecticides.
  • the invention provides use of a compound of formula I for control of insects of the family Curculionidae in useful plants.
  • the use may be for controlling Curculionidae that are resistant to one or more other insecticides.
  • the invention provides a method of controlling and/or preventing infestation of Anthonomus grandis in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I.
  • the Anthonomus grandis may be those that are resistant to one or more other insecticides.
  • the invention provides use of a compound of formula I for control of
  • Anthonomus grandis in useful plants The use may be for controlling Anthonomus grandis that are resistant to one or more other insecticides.
  • the invention provides a method of controlling and/or preventing infestation of
  • Anthonomus grandis in a crop of cotton comprising applying to a crop of cotton, the locus thereof, or propagation material thereof, a compound of formula I.
  • the Anthonomus grandis may be those that are resistant to one or more other insecticides.
  • the invention provides use of a compound of formula I for control of
  • Anthonomus grandis in cotton The use may be for controlling Anthonomus grandis that are resistant to one or more other insecticides.
  • Protection of a crop in a plot can be achieved by applying one or more pesticides to only a designated area of the plot.
  • the designated part of the plot is usually the outer most part of the plot, and is generally a border area of sufficient size that penetration of the insects/pests is prevented to the remaining part of the plot.
  • the benefit of spraying the border areas of the plot include a greater ability to control pest infestation because said insects/pests predominantly approach the plot from the periphery of the plot (i.e from the sides of the plot). There is also the benefit that a lower volume of active ingredient could be applied whilst still controlling the insects/pests pressure for the entire plot.
  • the designated plot part forms an outer border of the plot, which can uniformly encompass the remaining plot, but embodiments wherein the border is not uniform and wherein the border doesn't completely encompass the remaining plot is also envisaged provided the said insects/pests are controlled to an acceptable level in the plot. Further, the designated plot part doe not have to form the outer most part of the plot, but that is preferred to minimize the crop damage by the said insects/pests.
  • the area of the designated plot is of such size that acceptable control of the insects/pests is achieved. A skilled person would understand that a plot containing a crop would be applied with a number of pesticides during its growth.
  • the application of the pesticides to a designated plot can be applicable to all pesticide application, but would be more appropriate to those pesticides controlling those insects/pests that predominantly approach the plot from the periphery of the plot; accordingly, the remaining pesticides would be applied as normal, for example, throughout the plot.
  • pesticide A is for control of insects/pests that pests that predominantly approach the plot from the periphery of the plot while pesticide B is broad spectrum fungicide; therefore, pesticide A & B, either simultaneously or in any sequence, would be applied to the designated plot part (i.e a border region), while pesticide B would applied be applied throughout the plot.
  • the invention provides a method of protecting a plot of at least five hectares comprising a crop of useful plants, preferably cotton, susceptible to and/or under attack by insects/pests, preferably of the family Curculionidae, said method comprising applying to said plant and/or said insects/pests a compound of formula I in a pre-defined plot part that is between 0.5 to 20%, based on area, of the plot, provided said pre-defined plot part forms the outer border of the plot, wherein said insects/pests predominantly approach the plot from the periphery of the plot.
  • the pre-defined plot part that is applied with a compound of formula I is between 1 to 20%, based on area, of the plot, especially 5 to 15%.
  • the plot is between 5 to 10,000, such as at most 50 to 5,000, especially 100 to 1,000, particularly 150 to 500, hectares.
  • the invention provides a method for obtaining regulatory approval for the use of one or more of a compound of formula I to control, preferably in cotton, an insect of the family Curculionidae, in particular the species Anthonomus grandis, Conotrachelus nenuphar, Ceutorhynchus spp., or Curculio nucum, preferably Anthonomus grandis, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.
  • the compounds of the invention may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.
  • the compounds of the invention may contain one or more asymmetric carbon atoms, for example, at the C(#2)#3 group, and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
  • Reference to compounds of the invention also includes reference to salts and N-oxides.
  • cycle A, cycle B, cycle C, X, p, A 1 , A 2 , A 3 , A 4 , R 5 , R 7 and R 8 in compounds of formula I are, in any combination, as set out below.
  • cycle A is Ala.
  • cycle B is a cycle selected from cycle Bl, B2 and B3, more preferably cycle Bl or B2, most preferably cycle B 1.
  • In one group of compounds cycle B is Bl . In another group of compounds cycle B is B2. In another group of compounds cycle B is B3. In another group of compounds cycle B is B4. In another group of compounds cycle B is B5. In another group of compounds cycle B is B6.
  • cycle C is cycle CI
  • cycle C is 3,5-dichlorophenyl-, 3-chloro-4-fluorophenyl-, 3-fluoro-4- chlorophenyl-, 3,4-dichlorophenyl-, 3-chloro-4-bromophenyl-, 3,5-dichloro-4-fluorophenyl-, 3,4,5- trichlorophenyl-, 3,5-dichloro-4-iodophenyl-, 3,4,5-trifluorophenyl-, 3-chloro-5-bromophenyl-, 3-chloro- 5-fluorophenyl-, 3-chloro-5-(trifluoromethyl)phenyl-, 3,4-dichloro-5-(trifluoromethyl)phenyl-, 3,5- bis(trifluoromethyl)phenyl-, 4-chloro-3,5-bis(trifluoromethyl)phenyl-, 3-(trifluoromethyl)phenyl-, 2,6- dichloro-4-pyrid
  • a 1 is C-H or C-R 5 , most preferably A 1 is C-H.
  • a 2 is C-H or C-R 5 , most preferably A 2 is C-H.
  • a 3 is C-H or C-R 5 , most preferably A 3 is C-H.
  • a 4 is C-H or C-R 5 , most preferably A 4 is C-H.
  • a 1 and A 2 is nitrogen.
  • a 3 and A 4 is nitrogen.
  • a 1 and A 2 are both C-H.
  • both A 3 and A 4 are C-H
  • R 5 is methyl or chloro, most preferably methyl.
  • R 7 is trifluoromethyl.
  • each R 8 is independently fluoro, bromo or chloro.
  • p is 2 or 3, most preferably 2.
  • X is P2, P3 or P4.
  • cycle A is Ala
  • cycle B is Bl, B2 or B3
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • cycle A is Ala
  • cycle B is Bl
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • cycle A is Ala
  • cycle B is Bl
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • cycle A is Ala
  • cycle B is B2
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • cycle A is Ala
  • cycle B is B3
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • Table 1 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B 1 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 2 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B 1 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 3 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B 1 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 4 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B 1 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 5 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is Bl and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 6 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B 1 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 7 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 8 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 9 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 10 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 11 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 12 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 13
  • Table 13 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 14
  • Table 14 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 15
  • Table 15 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 16 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 17 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 18 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 19 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 20 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 21 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 22 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 23 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 24 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 25 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 26
  • Table 26 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 27
  • Table 27 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 28 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 29 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 30 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 31 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 32 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 33
  • Table 33 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 34 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 35 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 36 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 37 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 38 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 39 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 40 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B2, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 41 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B2, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 42 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B2, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 43 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B3, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 44 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B3, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 45 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B3, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 46 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B4, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 47 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B4, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 48 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B4, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 49 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B5, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 50 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B5, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 51 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B5, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 52 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B6, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 53 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B6, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • Table 54 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B6, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.
  • the compound of formula I is a compound selected from Tables 1 to 54.
  • Compounds of formula I where cycle B is selected from Bl to B6 include at least one chiral centre and may exist as compounds of formula I* (IA*, IB*, IC*, ID*, IE*, IF*) or compounds of formula I** (IA**, IB**, IC**, ID**, IE**, IF**).
  • the compounds of formula I** are more biologically active than the respective compounds of formula I*.
  • the invention includes mixtures of compounds I* and I** in any ratio e.g. in a molar ratio of 1 :99 to 99: 1, e.g. 10: 1 to 1 : 10, e.g. a substantially 50:50 molar ratio.
  • the molar proportion of compound I** compared to the total amount of both enantiomers is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.
  • the molar proportion of the compound of formula II* compared to the total amount of both enantiomers (or epimerically) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.
  • Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred.
  • Each compound disclosed in Tables 1 to 54 represents a specific disclosure of the isomer according to the compound of formula I* and the isomer according to the compound of formula I**, as indicated in the Tables, as well as mixtures enriched for the compound according to the compound of formula I*, and mixtures enriched for the compound according to the compound of formula I**, as described above.
  • the compounds of formula I may be prepared using the information provided in
  • WO2011/104089 and WO2011/154555 describe enantioselective routes to the compounds of formula I.
  • the compounds in Scheme 1 may be prepared according to the methods described in WO2011/104089.
  • the invention provides a compound selected from Tables 1 to 6 for use aga ainst insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 7 to 12 for use aga ainst insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 13 to 18 for use aga ainst insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 19 to 24 for use against insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 25 to 30 for use ag aainst insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 31 to 36 for use ag aainst insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 37 to 39 for use ag aainst insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 40 to 42 for use against insects of the family Curculionidae, preferably in for use against Anthonomus grandis. In one embodiment the invention provides a compound selected from Tables 43 to 45 for use against insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 46 to 48 for use against insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 49 to 51 for use against insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 52 to 54 for use against insects of the family Curculionidae, preferably in for use against Anthonomus grandis.
  • the invention provides a compound selected from Tables 1 to 6 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 7 to 12 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 13 to 18 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 19 to 24 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 25 to 30 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 31 to 36 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 37 to 39 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 40 to 42 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 43 to 45 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 46 to 48 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 49 to 51 for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 52 to 54 for use against Anthonomus grandis in cotton.
  • insects from the family of Curculionidae we Anthonomus corvulus, Anthonomus elutus, Anthonomus elongatus, Anthonomus eugenii, Anthonomus consors, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus,
  • insects from the family of Curculionidae are of the genus Anthonomus, preferably of the species Anthonomus grandis,
  • Conotrachelus nenuphar, Ceutorhynchus spp., or Curculio nucum more preferably of the species Anthonomus grandis.
  • the methods and uses of the invention are for controlling and/or preventing infestation of a cotton crop by Anthonomus grandis (commonly known as boll weevil) including
  • Anthonomus grandis that is resistant to other insecticides e.g. pyrethroid insecticides.
  • Anthonomus grandis that is "resistant" to a particular insecticide refers e.g. to strains of Anthonomus grandis that are less sensitive to that insecticide compared to the expected sensitivity of the same species of Anthonomus grandis.
  • the expected sensitivity can be measured using e.g. a strain that has not previously been exposed to the insecticide.
  • the methods and uses of the invention are for controlling lepidopteran leaf feeders, bollworms, bollweevil, aphids, whitefly, thrips, lygus, mites, cutworms, soil insects, and/or nematodes.
  • the compounds of the invention may be used on cotton to control, for example, Anthonomus grandis, Pectinophora spp., heliothis spp., Spodoptera spp., Tetranychus spp., Empoasca spp., Thrips spp., Bemisia tabaci, Trialeurodes spp., Aphids, Lygus spp., phyllophaga spp., Scaptocoris spp., Austroasca viridigrisea, Creontiades spp., Nezara spp., Piezodorus spp., Halotydeus destructor, Oxycaraenus hyalinipennis, Dysdercus cingulatus.
  • Anthonomus grandis Pectinophora spp., heliothis spp., Spodoptera spp., Tetranychus spp., Empoasca spp
  • the compounds of the invention are used on cotton to control Anthonomus grandis, Tetranychus spp., Empoasca spp., thrips spp., Lygus spp., phyllophaga spp., Scaptocoris spp..
  • locus of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil.
  • An example for such a locus is a field, on which crop plants are growing.
  • plant propagation material is understood to denote generative parts of a plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material” is understood to denote seeds.
  • 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. However, control of Anthonomus grandis s is usually achieved by foliar application, which is the preferred mode of application according to the invention.
  • Application of the compounds of the invention is preferably to a crop of cotton plants, the locus thereof or propagation material thereof.
  • Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Treatment according to the invention of the plants and plant parts with the active compounds can be carried out directly or by allowing the compounds to act on their surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injecting and, in the case of propagation material, in particular in the case of seed, also by applying one or more coats.
  • the compounds of the invention are suitable for use on any plant (preferably cotton plant), 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.
  • plants as used herein includes seedlings, bushes and trees. Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering.
  • herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate- resistant maize varieties commercially available under the trade names RoundupReady® and
  • Compounds of formula I may be used on transgenic plants (including cultivars) obtained by genetic engineering methods and/or by conventional methods. These are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.
  • 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 modification, 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 temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, 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.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Transgenic cotton is of particular interest.
  • Pesticidal proteins may be used on transgenic plants that are capable of producing one or more pesticidal proteins which confer upon the transgenic plant tolerance or resistance to harmful pests, e.g. insect pests, nematode pests and the like.
  • pesticidal proteins include, without limitation, Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105; or vegetative insecticidal proteins such as Vipl, Vip2 or Vip3.
  • Bt Cry proteins and VIPs useful in the invention can be found on the worldwide web at Bacillus thuringiensis Toxin Nomenclature Database maintained by the University of Wales ⁇ see also, Crickmore et al. (1998) Microbiol. Mol. Biol. Rev. 62:807-813).
  • Other pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp.
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome- inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl -transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium or calcium
  • pesticidal proteins or transgenic plants capable of synthesizing such proteins are disclosed, e.g., in EP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 and WO 03/52073.
  • Agrisure®CB (PI) (corn producing CrylAb), Agrisure®RW (P2) (corn producing mCry3A), Agrisure® Viptera (P3) (corn hybrids producing Vip3Aa); Agrisure300GT (P4) (corn hybrids producing Cryl Ab and mCry3A); YieldGard® (P5) (corn hybrids producing the Cryl Ab protein), YieldGard® Plus (P6) (corn hybrids producing CrylAb and Cry3Bbl), Genuity® SmartStax® (P7) (corn hybrids with CrylA.105, Cry2Ab2, CrylF, Cry34/35, Cry3Bb) ; Herculex® I (P8) (corn hybrids producing CrylFa) and Herculex®RW (P9) (corn hybrids producing Cry34Abl, Cry35Abl and the enzyme Phosphinothricin-N-
  • transgenic crops are:
  • Btl 76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 7). Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer ⁇ Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylA(b) toxin. Btl 76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 8). Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/DE/02/9 (P19). MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,
  • NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • transgenic plants and of very high interest, are those carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g. WO 2011066384) (, glyphosate (e.g. Roundup Ready® (P24), Roundup Ready 2 Yield® (P25)), sulfonylurea (e.g. STS®) (P26), glufosinate (e.g. Liberty Link® (P27), Ignite® (P28)), Dicamba (P29) (Monsanto), HPPD tolerance (P30) (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta).
  • Enlist® e.g. WO 2011066384
  • glyphosate e.g. Roundup Ready® (P24), Roundup Ready 2 Yield® (P25)
  • sulfonylurea e.g. STS®
  • P26 glufosinate
  • P27 glufos
  • Double or triple stacks of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance ((e.g. Optimum GAT®) (P31), plants stacked with STS® and Roundup Ready® (P32) or plants stacked with STS® and Roundup Ready 2 Yield® (P33)), dicamba and glyphosate tolerance (P34) (Monsanto).
  • glyphosate and sulfonyl-urea tolerance (e.g. Optimum GAT®) (P31), plants stacked with STS® and Roundup Ready® (P32) or plants stacked with STS® and Roundup Ready 2 Yield® (P33)), dicamba and glyphosate tolerance (P34) (Monsanto).
  • soybean plants carrying trains conferring resistance to 2.4D e.g. Enlist®
  • glyphosate e.g. Roundup Ready®, Roundup Ready 2 Yield®
  • HPPD tolerance e.g. isoxaflutole herbicide
  • cotton transgenic events examples include
  • GHB614 (FibreMax GlyTol cotton ®- BCS Stoneville)
  • GHB614 x LL25 (FibreMax LL GlyTol cotton ® - BCS Stoneville)
  • 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 suitable for use on any cotton plant, 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, e.g. BT cotton.
  • a compound of the invention may be used 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.
  • the invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of the invention.
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate.
  • a pesticide e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate.
  • An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components.
  • suitable pesticides include the following:
  • a) Pyrethroids such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin and gamma cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox or
  • Organophosphates such as profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s -methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb,
  • Benzoyl ureas such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron or chlorfluazuron;
  • Organic tin compounds such as cyhexatin, fenbutatin oxide or azocyclotin;
  • Pyrazoles such as tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate;
  • Macrolides such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad, azadirachtin, milbemectin, lepimectin or spinetoram;
  • Organochlorine compounds such as endosulfan (in particular alpha-endosulfan), benzene hexachloride, DDT, chlordane or dieldrin;
  • Amidines such as chlordimeform or amitraz
  • Fumigant agents such as chloropicrin, dichloropropane, methyl bromide or metam
  • Neonicotinoid compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, or nithiazine;
  • Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide
  • Diphenyl ethers such as diofenolan or pyriproxifen
  • Ketoenols such as Spirotetramat, spirodiclofen or spiromesifen
  • Diamides such as flubendiamide, chlorantraniliprole (Rynaxypyr®) or cyantraniliprole;

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

La présente invention concerne des procédés qui consistent à appliquer sur une culture de cottoniers, sur le lieu d'une telle culture ou sur une matière de propagation de celle-ci, un composé représenté par la formule I. Dans la formule, le cycle A représente A1a ou A2a ; A1, A2, A3 et A4 représentent indépendamment C-H ou un azote, #1 représentant la liaison à X et #2 représentant la liaison au cycle B ; le cycle B est sélectionné dans le groupe comprenant B1 à B6, #1 représentant la liaison au cycle A, #2 représentant la liaison à R7 et #3 représentant la liaison au cycle C ; le cycle C représente un phényle ; R5 représente un groupe chloro, bromo, CF3 ou méthyle ; R7 représente un chlorodifluorométhyle ou un trifluorométhyle ; chaque R8 représente indépendamment un groupe bromo, chloro, fluoro ou trifluorométhyle ; p représente 1, 2 ou 3; et X est sélectionné dans le groupe comprenant P1 à P9. Les procédés servent de préférence à lutter contre et/ou à prévenir une infestation d'insectes de la famille des curculionidés, en particulier Anthonomus grandis.
PCT/EP2013/062901 2012-06-21 2013-06-20 Procédés de lutte contre des insectes WO2013190050A1 (fr)

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Cited By (1)

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JP2017509693A (ja) * 2014-02-03 2017-04-06 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 無脊椎有害生物防除用シクロペンテン化合物及びシクロペンタジエン化合物

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WO2010020522A1 (fr) * 2008-08-22 2010-02-25 Syngenta Participations Ag Composés insecticides
WO2010149506A1 (fr) * 2009-06-22 2010-12-29 Syngenta Participations Ag Composés insecticides
WO2011101229A1 (fr) * 2010-02-22 2011-08-25 Syngenta Participations Ag Derives de dihydrofurane utilises comme composes insecticides
WO2012045700A1 (fr) * 2010-10-05 2012-04-12 Syngenta Participations Ag Pyrolidin-yl-aryl-carboxamides insecticides

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WO2009080250A2 (fr) * 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
WO2010020522A1 (fr) * 2008-08-22 2010-02-25 Syngenta Participations Ag Composés insecticides
WO2010149506A1 (fr) * 2009-06-22 2010-12-29 Syngenta Participations Ag Composés insecticides
WO2011101229A1 (fr) * 2010-02-22 2011-08-25 Syngenta Participations Ag Derives de dihydrofurane utilises comme composes insecticides
WO2012045700A1 (fr) * 2010-10-05 2012-04-12 Syngenta Participations Ag Pyrolidin-yl-aryl-carboxamides insecticides

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Publication number Priority date Publication date Assignee Title
JP2017509693A (ja) * 2014-02-03 2017-04-06 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 無脊椎有害生物防除用シクロペンテン化合物及びシクロペンタジエン化合物
US10407383B2 (en) 2014-02-03 2019-09-10 Basf Se Cyclopentene and cyclopentadiene compounds for controlling invertebrate pests

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