WO2013190046A1 - Procédés de lutte contre des parasites du sol - Google Patents

Procédés de lutte contre des parasites du sol Download PDF

Info

Publication number
WO2013190046A1
WO2013190046A1 PCT/EP2013/062897 EP2013062897W WO2013190046A1 WO 2013190046 A1 WO2013190046 A1 WO 2013190046A1 EP 2013062897 W EP2013062897 W EP 2013062897W WO 2013190046 A1 WO2013190046 A1 WO 2013190046A1
Authority
WO
WIPO (PCT)
Prior art keywords
cycle
phenyl
compound
formula
trifluoromethyl
Prior art date
Application number
PCT/EP2013/062897
Other languages
English (en)
Inventor
Myriem El Qacemi
Jérôme Yves CASSAYRE
Benedikt KURTZ
Original Assignee
Syngenta Participations Ag
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 Syngenta Participations Ag filed Critical Syngenta Participations Ag
Publication of WO2013190046A1 publication Critical patent/WO2013190046A1/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
    • A01N43/34—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 methods of soil pest control and in particular to control of corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante.
  • GABA gamma-aminobutyric acid
  • GABA gamma- aminobutyric acid
  • WO2009/080250 corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante.
  • the compounds of interest include a thietane amide derivative in which the thietane carbon ring members are unsubstituted.
  • the invention provides a method of controlling and/or preventing soil-dwelling pests in useful plants comprising applying to the locus of the useful plant or treating propagation material thereof, la I
  • 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 use of a compound of formula I for the control of a soil- dwelling pest in useful plants.
  • the soil-dwelling pest is selected from corn rootworm, wireworms, grubs, in particular white grubs (e.g. Phyllophaga sp., Diloboderus sp., Popillia japonica), termites (in particular for sugar cane), subterraneous stinkbugs (e.g. Scaptocoris sp.) , cutworms (e.g. agrotis sp.), millipedes (e.g. Julus sp.) and broca gigante (e.g. Telchin licus).
  • white grubs e.g. Phyllophaga sp., Diloboderus sp., Popillia japonica
  • termites in particular for sugar cane
  • subterraneous stinkbugs e.g. Scaptocoris sp.
  • cutworms e.g. agrotis sp.
  • millipedes e.g. Julus
  • the invention provides a method of controlling and/or preventing corn rootworm in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides a method of controlling and/or preventing wireworms in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides a method of controlling and/or preventing grubs, in particular white grubs, in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides a method of controlling and/or preventing
  • Phyllophaga sp. in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides a method of controlling and/or preventing
  • Diloboderus sp. in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides a method of controlling and/or preventing Popillia japonica in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides a method of controlling and/or preventing termites (in particular for sugar cane) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides a method of controlling and/or preventing subterraneous stinkbugs (e.g. Scaptocoris sp.) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • subterraneous stinkbugs e.g. Scaptocoris sp.
  • the invention provides a method of controlling and/or preventing cutworms (e.g. agrotis sp.) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • cutworms e.g. agrotis sp.
  • the invention provides a method of controlling and/or preventing millipedes
  • the invention provides a method of controlling and/or preventing broca gigante (e.g. Telchin licus) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • broca gigante e.g. Telchin licus
  • the invention provides a method of improving the growth of useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.
  • the invention provides use of a compound of formula I as defined in claims 1 for improving the growth of useful plants.
  • the invention provides a method comprising applying a compound of formula I to the locus of corn plants by direct soil application.
  • a compound of formula I is Ala
  • cycle B is Bl
  • B2 preferably B 1
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to the locus of corn plants by direct soil application.
  • a compound of formula I Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R 7 is trifluoromethyl and X is P2, P3 or P4.
  • the invention provides a method comprising applying a compound of formula I to the locus of corn plants by in-furrow application.
  • a compound of formula I Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R 7 is trifluoromethyl and X is P2, P3 or P4.
  • the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to the locus of corn plants by direct soil application.
  • a compound of formula I Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R 7 is trifluoromethyl and X is P2, P3 or P4.
  • the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to the locus of corn plants by in- furrow application.
  • a compound of formula I Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R 7 is trifluoromethyl and X is P2, P3 or P4.
  • the invention provides a method of controlling and/or preventing corn rootworm in useful plants comprising applying a compound of formula I to the locus of the useful plants by direct soil application.
  • a compound of formula I is Ala
  • cycle B is Bl
  • B2 preferably B 1
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • the invention provides a method of controlling and/or preventing corn rootworm in useful plants comprising applying a compound of formula I to the locus of the useful plants by in-furrow application.
  • a compound of formula I is Ala
  • cycle B is Bl, or B2, preferably B 1
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • the invention provides use of a compound of formula I for controlling and/or preventing corn rootworm in useful plants, preferably corn plants, by applying a compound of formula I to the locus of the useful plants directly to soil.
  • Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R 7 is trifluoromethyl and X is P2, P3 or P4.
  • the invention provides use of a compound of formula I for controlling and/or preventing corn rootworm in useful plants, preferably corn rootworm, by applying a compound of formula I to the locus of the useful plants and appliying the compound of formula I by in- furrow application.
  • a compound of formula I for controlling and/or preventing corn rootworm in useful plants, preferably corn rootworm, by applying a compound of formula I to the locus of the useful plants and appliying the compound of formula I by in- furrow application.
  • Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R 7 is trifluoromethyl and X is P2, P3 or P4.
  • the invention provides a method comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I directly to soil.
  • a compound of formula I is Ala
  • cycle B is Bl
  • B2 preferably Bl
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • the invention provides a method comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I by in-furrow application.
  • a compound of formula I is Ala
  • cycle B is Bl
  • B2 preferably Bl
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I directly to soil.
  • Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R 7 is trifluoromethyl and X is P2, P3 or P4.
  • the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I by in-furrow application.
  • a compound of formula I is Ala
  • cycle B is Bl
  • B2 preferably Bl
  • cycle C is phenyl
  • R 7 is trifluoromethyl
  • X is P2, P3 or P4.
  • Application before planning includes e.g. up to 1, 2, 3, 4, 5, or even up to 10 days before planting.
  • Application after planting includes e.g. up to 1, 2, 3, 4, 5, or even up to 10 days after planting.
  • application may be up to 10 days before or after planting, preferably up to 5 days before or after planting, more preferably up to up to 2 days before or after planting, most preferably up to 1 day before or after planting.
  • Seed treatment is an example of indirect application to soil, e.g. the application of the compound of formula I by direct soil application comprises applying the compound of formula I to the soil other than via seed treatment.
  • the invention provides a method for obtaining regulatory approval for the use of one or more of a compound of formula I to control a pest selected from corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante, 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-, more preferably 3-chloro-5-brom
  • 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.
  • no more than one of A 1 and A 2 is nitrogen.
  • no more than one of 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 trifiuoromethyl.
  • 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
  • cycle C is phenyl
  • cycle A is Ala
  • cycle B is Bl
  • cycle C is phenyl
  • R 7 is trifiuoromethyl.
  • cycle A is Ala
  • cycle B is Bl
  • cycle C is phenyl
  • R 7 is trifiuoromethyl
  • X is P2, P3 or P4.
  • cycle A is Ala
  • cycle B is Bl
  • cycle C is phenyl
  • R 7 is trifiuoromethyl
  • X is P2, P3 or P4.
  • cycle A is Ala
  • cycle B is B2
  • cycle C is phenyl
  • R 7 is trifiuoromethyl
  • X is P2, P3 or P4.
  • cycle A is Ala
  • cycle B is B3
  • cycle C is phenyl
  • R 7 is trifiuoromethyl
  • 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 trifiuoromethyl, 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 trifiuoromethyl, 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 trifiuoromethyl, 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 trifiuoromethyl, 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 B 1 and R7 is trifiuoromethyl, 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 trifiuoromethyl, 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 trifiuoromethyl, and cycle C and X are as defined in Table P.
  • Table 8
  • 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
  • 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 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 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 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
  • 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
  • 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 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 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.
  • cycle A is cycle Ala
  • R5 is methyl
  • Al and A2 are CH-CH
  • Cycle B is B6 and R7 is trifluoromethyl
  • 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
  • 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.
  • Soil-dwelling pest refers to a pest that causes plant damage whilst in a life cycle phase that lives in the soil, and for example, damages plant roots. Examples of specific pests are described below. Soil dwelling pests may be insects, acarines and/or nematodes, preferably insects, or acarines, most preferably insects.
  • 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.
  • Table Q provides 792 preferred substituent combinations for the compounds illustrated in Scheme 1 Table 0
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing soil pests. In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing corn rootworm.
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing wire worms. In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing wire worms.
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing grubs, in particular white grubs. In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing Phyllophaga sp..
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing Diloboderus sp.. In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing Diloboderus sp..
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing Popillia japonica. In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing Popillia japonica.
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing termites, e.g. for sugarcane.
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp.. In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..
  • the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing cutworms, e.g. agrotis sp..
  • the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing cutworms, e.g. agrotis sp..
  • the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des procédés de lutte et/ou de prévention contre des parasites vivant dans le sol chez des végétaux utiles. Ces procédés consistent à appliquer sur le lieu où pousse le végétal utile un composé représenté par la formule (I), ou à traiter une matière de propagation dudit végétal à l'aide d'un tel composé. Dans la formule, le cycle A représente A1a ou A2a, A1, A2, A3 et A4 représentant 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 un 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.
PCT/EP2013/062897 2012-06-21 2013-06-20 Procédés de lutte contre des parasites du sol WO2013190046A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12172965.1 2012-06-21
EP12172965 2012-06-21

Publications (1)

Publication Number Publication Date
WO2013190046A1 true WO2013190046A1 (fr) 2013-12-27

Family

ID=48699009

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/062897 WO2013190046A1 (fr) 2012-06-21 2013-06-20 Procédés de lutte contre des parasites du sol

Country Status (2)

Country Link
AR (1) AR091513A1 (fr)
WO (1) WO2013190046A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Also Published As

Publication number Publication date
AR091513A1 (es) 2015-02-11

Similar Documents

Publication Publication Date Title
AU2013305200B2 (en) Methods of soil pest control
US9474279B2 (en) Methods of controlling insects
US20230320357A1 (en) Methods of pest control in soybean
US20130317073A1 (en) Methods of pest control in soybean
US9320278B2 (en) Methods of controlling insects
EP2887802A2 (fr) Procédés de lutte contre les nuisibles vivant dans le sol
WO2014029706A2 (fr) Procédés de lutte contre les insectes
WO2014029708A1 (fr) Procédés de contrôle des insectes
WO2013190050A1 (fr) Procédés de lutte contre des insectes
WO2014019951A1 (fr) Méthodes de lutte contre les insectes
WO2014131837A1 (fr) Dérivés de l'isoxaline à utiliser sur des plants de coton
WO2013190046A1 (fr) Procédés de lutte contre des parasites du sol
WO2014019957A2 (fr) Procédés de lutte antiparasitaire dans du soja
WO2014029707A1 (fr) Procédés de lutte contre les insectes

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: 13731315

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: 13731315

Country of ref document: EP

Kind code of ref document: A1