DK2507230T3 - Insekticidforbindelser baseret på isoxazolinderivater - Google Patents

Insekticidforbindelser baseret på isoxazolinderivater Download PDF

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DK2507230T3
DK2507230T3 DK10787393.7T DK10787393T DK2507230T3 DK 2507230 T3 DK2507230 T3 DK 2507230T3 DK 10787393 T DK10787393 T DK 10787393T DK 2507230 T3 DK2507230 T3 DK 2507230T3
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compound
methyl
formula
alkyl
phenyl
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DK10787393.7T
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Jérôme Yves Cassayre
Peter Renold
Qacemi Myriem El
Thomas Pitterna
Julie Clementine Toueg
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Syngenta Participations Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Claims (16)

1. Forbindelse med formel (I):
hvor A1, A2, A3 og A4 uafhængigt af hinanden er C-H, C-R5 eller nitrogen; G1 er oxygen eller svovl; L er en enkeltbinding eller Ci-Csalkylen; R1 er hydrogen, Ci-Csalkyl, Ci-Csalkylcarbonyl-, Ci-Csalkoxy, Ci-Csalkoxy-Ci-Csalkyl eller Ci-Csalkoxycarbonyl-; R2 er hydrogen, Ci-Cshalogenalkyl eller Ci-Csalkyl; R3 er Ci-Cshalogenalkyl; R4 er aryl eller aryl substitueret med en til tre R6, eller R4 er heterocyclyl eller heterocyclyl substitueret med en til tre R6; hver R5 uafhængigt er halogen, cyano, nitro, Ci-Csalkyl, C3-Cecycloalkyl, Ci-Cehalogenalkyl, C2-Csalkenyl, C2- Cshalogenalkenyl, C2-Csalkynyl, C2-Cshalogenalkynyl, Ci-Csalkoxy, Ci-Cshalogenalkoxy, Ci-Csalkoxycarbonyl-, eller to R5 på tilstødende carbonatomer sammen danner en -CH=CH-CH=CH- bro eller en -N=CH-CH=CH- bro; hver R6 uafhængigt er halogen, cyano, nitro, Ci-Csalkyl, Ci-Cshalogenalkyl, Ci-Csalkoxy eller Ci-Cshalogenalkoxy; Y1 er CR7R8, Y2 er 0, Y3 er N-R9, og Y4 er C=0; hver R7 og R8 er uafhængigt hydrogen, halogen, Ci-Csalkyl eller Ci-Cshalogenalkyl; hver R9 uafhængigt er hydrogen, cyano, cyano-Ci-Csalkyl, Ci-Csalkyl, Ci-Cshalogenalkyl, Cs-Cscycloalkyl, Cs-Cscycloalkyl, hvor ét carbonatom er erstattet af 0, S, S (0) eller SO2, eller C3-Cscycloalkyl-Ci-Csalkyl, Cs-Cscycloalkyl-Ci-Csalkyl, hvor ét carbonatom i cycloalkylgruppen er erstattet af 0, S, S (0) eller SO2, eller Cs-Cscycloalkyl-Ci-Cshalogenalkyl, Ci-Cshydroxyalkyl, Ci-C8alkoxy-Ci-C8alkyl, C2-Csalkenyl, C2-Cshalogenalkenyl, C2- Csalkynyl, C2-Cshalogenalkynyl, phenyl, phenyl substitueret med en til tre R10, phenyl-Ci-C4alkyl, phenyl-Ci-C4alkyl, hvor phenyldelen er substitueret med en til tre R10, en 5-6-leddet heteroaryl-Ci~C4alkyl eller en 5-6-leddet heteroaryl-Ci-C4alkyl, hvor heteroaryldelen er substitueret med en til tre R10, Ci-C4alkyl- (Ci-C4alkyl-0-N=) C-CH2-; hver R10 uafhængigt er halogen, cyano, nitro, Ci-Csalkyl, Ci-Cshalogenalkyl, Ci-Csalkoxy eller Ci-Cshalogenalkoxy; eller et salt eller en N-oxid deraf.
2. Forbindelse ifølge krav 1, hvor forbindelsen er en forbindelse med formel (Ia.E):
3. Forbindelse ifølge krav 1 eller krav 2, hvor A1 er C-R5, A2 er C-H, A3 er C-H, A4 er C-H.
4. Forbindelse ifølge et hvilket som helst af kravene 1 til 3, hvor R3 er chlordifluormethyl eller trifluormethyl.
5. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, hvor R4 er phenyl substitueret med en til tre R6.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor R5 er brom, chlor, fluor, cyclopropyl, vinyl eller methyl.
7. Forbindelse ifølge et hvilket som helst af kravene 1 til 6, hvor hver R6 uafhængigt er chlor, fluor, cyano, nitro, methyl, ethyl, trifluormethyl, methoxy eller trifluormethoxy.
8. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor R9 er hydrogen, cyano-Ci-Csalkyl, Ci-Cealkyl, C3-Cecycloalkyl, Cs-Cscycloalkyl, hvor ét carbonatom i cycloalkylgruppen er erstattet af 0, S, S (0) eller SO2, eller Ci-Cshalogenalkyl, Ci-Cshydroxyalkyl, C2-C8alkenyl, C2-C8alkynyl, phenyl - Ci-C4 al kyl eller phenyl-Ci-C4alkyl, hvor phenyldelen er substitueret med en til tre R10, en 5-6-leddet heteroaryl-Ci-C4alkyl eller en 5-6-leddet heteroaryl-Ci-C4alkyl, hvor heteroaryldelen er substitueret med en til tre R10, og hvor heteroaryl er pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl eller thiazolyl.
9. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor R9 er hydrogen, Ci-C4alkyl, C3-C6cycloalkyl, Ci- C4halogenalkyl, Ci-C4hydroxyalkyl, Ci-C4alkoxy-Ci-C4alkyl, phenyl-CH2-alkyl- eller phenyl-CH2-, hvor phenyldelen er substitueret med en til tre R10, furanyl eller furanyl, der er substitueret med en til tre R10, thietanyl, oxetanyl, oxothietanyl eller dioxothietanyl.
10. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor R9 er methyl, ethyl, cyclopropyl, cyclobutyl, oxetanyl, thietanyl, trifluorethyl, difluorethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substitueret med en til tre R10 eller pyridinmethyl- eller pyridinmethyl- substitueret med en til tre R10.
11. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor R9 er ethyl eller trifluorethyl.
12. Forbindelse ifølge krav 1, hvor forbindelsen med formel I er en forbindelse med formel B5 eller B6:
eller en forbindelse med formel Cl, C2, C3, C4, C5, C8 eller C9:
eller en forbindelse med formel E2:
eller en forbindelse med formel GI, G3, G5 eller G6:
13. Forbindelse med formel (Int-I)
hvor A1, A2, A3, A4, G1, L, R1, R2, Y1, Y2, Y3 og Y4 er som defineret for en forbindelse med formel (I) ifølge et hvilket som helst af kravene 1 til 11, og XB er en brom, eller XB er cyano, formyl, CH=N-OH eller acetyl; eller et salt eller en N-oxid deraf; eller en forbindelse med formel (Int-II)
hvor A1, A2, A3, A4, G1, L, R1, R2, Y1, Y2, Y3 og Y4 er som defineret for en forbindelse med formel (I) ifølge et hvilket som helst af kravene 1 til 11, og Xc er Cth-halogen, CH=C(R3)R4 eller CH2C (OH) (R3) R4, hvor R3 og R4 er som defineret for en forbindelse med formel (I) ifølge et hvilket som helst af kravene 1 til 11; eller et salt eller en N-oxid deraf.
14. Fremgangsmåde til bekæmpelse af et angreb af hvirvelløse skadedyr, som omfatter påføring på skadedyret, på en locus for skadedyret eller på en plante, der er modtagelig for angreb af skadedyret, af en pesticidvirkende effektiv mængde af en forbindelse med formel (I) som defineret i et hvilket som helst af kravene 1 til 12, hvor fremgangsmåden ikke er en fremgangsmåde til behandling af menneske- eller dyrekroppen.
15. Sammensætning, der omfatter en pesticidvirkende effektiv mængde af en forbindelse med formel (I) som defineret i et hvilket som helst af kravene 1 til 11 og eventuelt omfatter en yderligere pesticidaktiv bestanddel.
16. Sammensætning ifølge krav 15, hvor den yderligere pesticidaktive bestanddel er valgt blandt a) Pyrethroider valgt blandt permethrin, cypermethrin, fenvalerat, esfenvalerat, deltamethrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, naturlig pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin og 5-benzyl-3-furylmethyl-(E)-(IR,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenmethyl)cyclopropancarboxylat; b) Organophosphater valgt blandt profenofos, sulprofos, acephat, methylparathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoat, phosphamidon, malathion, chlorpyrifos, phosalon, terbufos, fensulfothion, fonofos, phorat, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazat og diazinon; c) Carbamater (herunder arylcarbamater) valgt blandt pirimicarb, triazamat, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl og oxamyl; d) Benzoylurinstoffer valgt blandt diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, lufeneron og chlorfluazuron; f) Organiske tinforbindelser valgt blandt cyhexatin, fenbutatinoxid og azocyclotin; f) Pyrazoler valgt blandt tebufenpyrad og fenpyroximat; g) Makrolider valgt blandt abamectin, emamectinbenzoat, ivermectin, milbemycin, spinosad, azadirachtin og spinetoram; i) Organochlorforbindelser valgt blandt endosulfan, alfa-endosulfan, benzenhexachlorid, DDT, chlordan og dieldrin; j) Amidiner valgt blandt chlordimeform og amitraz; k) Fumigeringsmidler valgt blandt chloropicrin, dichloropropan, methylbromid og metam; l) Neonicotinoidforbindelser valgt blandt imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, nithiazin og flonicamid; m) Diacylhydraziner valgt blandt tebufenozid, chromafenozid og methoxyfenozid; n) Diphenylethere valgt blandt diofenolan og pyriproxifen; o) Indoxacarb; p) Chlorfenapyr; q) Pymetrozin; r) Spirotetramat, spirodiclofen og spiromesifen; s) Diamider valgt blandt flubendiamid, chlorantraniliprol og cyantraniliprol; t) Sulfoxaflor; u) Metaflumizon; v) Fipronil og ethiprol; w) Pyrifluqinazon; x) Buprofezin; y) 4-[(6-chlorpyridin-3-ylmethyl)-(2,2-difluorethyl)-amino]-5H-furan-2-on; og fungicidforbindelser valgt blandt (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl) phenyl]-2-methoxyiminoacetamid (SSF-129) , 4-brom-2-cyano-i\7, i7-dimethyl-6- trifluormethylbenzimidazol-l-sulfonamid, a-[N-(3-chlor-2,6- xylyl) -2-methoxyacetamido] -γ-butyrolacton, 4-chlor-2-cyano-i\7, dimethyl-5-p-tolylimidazol-1-sulfonamid (IKF-916, cyamidazosulfamid) , 3, 5-dichlor-iV- (3-chlor-l-ethyl-l-methyl-2- oxopropyl)-4-methylbenzamid (RH-7281, zoxamid), W-allyl-4,5, -dimethyl-2-trimethylsilylthiophen-3-carboxamid (MON65500), N-(1-cyano-1,2-dimethylpropy1)-2-(2,4-dichlorphenoxy)propionamid (AC382042), N-(2-methoxy-5-pyridyl)-cyclopropancarboxamid, acibenzolar (CGA245704) (f.eks. acibenzolar-S-methyl), alanycarb, aldimorph, anilazin, azaconazol, azoxystrobin, benalaxyl, benomyl, benthiavalicarb, biloxazol, bitertanol, bixafen, blasticidin S, boscalid, bromuconazol, bupirimat, captafol, captan, carbendazim, carbendazimchlorhydrat, carboxin, carpropamid, carvon, CGA41396, CGA41397, chinomethionat, chlorothalonil, chlorozolinat, clozylacon, kobberholdige forbindelser valgt blandt kobberoxychlorid, kobberoxyquinolat, kobbersulfat, kobbertallat og bordeauxvæske, cyclufenamid, cymoxanil, cyproconazol, cyprodinil, debacarb, di-2-pyridyldisulfid-1,1'-dioxid, dichlofluanid, diclomezin, dicloran, diethofencarb, difenoconazol, difenzoquat, diflumetorim, O, O-di-iso-propyl-S-benzylthiophosphat, dimefluazol, dimetconazol, dimethomorph, dimethirimol, diniconazol, dinocap, dithianon, dodecyldimethylammoniumchlorid, dodemorph, dodin, doguadin, edifenphos, epoxiconazol, ethirimol, ethyl-(Z,) -N-benzyl-N-([methyl(methylthioethylidenaminooxycarbonyl) amino]thio)-β-alaninat, etridiazol, famoxadon, fenamidon (RPA407213), fenarimol, fenbuconazol, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, fenpropimorph, fentinacetat, fentinhydroxid, ferbam, ferimzon, fluazinam, fludioxonil, flumetover, fluopyram, fluoxastrobin, fluoroimid, fluquinconazol, flusilazol, flutolanil, flutriafol, fluxapyroxad, folpet, fuberidazol, furalaxyl, furametpyr, guazatin, hexaconazol, hydroxyisoxazol, hymexazol, imazalil, imibenconazol, iminoctadin, iminoctadintriacetat, ipconazol, iprobenfos, iprodion, iprovalicarb (SZX0722), isopropanylbutylcarbamat, isoprothiolan, isopyrazam, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamid, maneb, mefenoxam, metalaxyl, mepanipyrim, mepronil, metalaxyl, metconazol, metiram, metiram-zink, metominostrobin, myclobutanil, neoasozin, nikkeldimethyldithiocarbamat, nitrothal-isopropyl, nuarimol, ofurace, organokviksølvforbindelser, oxadixyl, oxasulfuron, oxolinsyre, oxyconazol, oxycarboxin, pefurazoat, penconazol, pencycuron, penflufen, penthiopyrad, phenazinoxid, phosetyl-Al, phosphorsyrer, phthalid, picoxystrobin (ZA1963), polyoxin D, polyram, probenazol, prochloraz, procymidon, propamocarb, propiconazol, propineb, propionsyre, prothioconazol, pyrazophos, pyrifenox, pyrimethanil, pyraclostrobin, pyroquilon, pyroxyfur, pyrrolnitrin, kvaternære ammoniumforbindelser, quinomethionat, quinoxyfen, quintozen, sedaxan, sipconazol (F-155), natriumpentachlorphenat, spiroxamin, streptomycin, svovl, tebuconazol, tecloftalam, tecnazen, tetraconazol, thiabendazol, thifluzamid, 2-(thiocyanomethylthio)benzothiazol, thiophanat-methyl, thiram, timibenconazol, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxid, tricyclazol, tridemorph, trifloxystrobin (CGA279202), triforin, triflumizol, triticonazol, validamycin A, vapam, vinclozolin, zineb og ziram, 1,3-dimethyl-lH-pyrazol-4-carboxylsyre-(4'- methylsulfanylbiphenyl-2-yl)-amid, 1,3-dimethyl-lH-pyrazol-4-carboxylsyre-(2-dichlormethylen-3-ethyl-l-methylindan-4-yl)-amid og 1,3-dimethyl-4H-pyrazol-4-carboxylsyre-[2-(2,4-dichlorphenyl)-2-methoxy-l-methylethyl]-amid.
DK10787393.7T 2009-12-01 2010-12-01 Insekticidforbindelser baseret på isoxazolinderivater DK2507230T3 (da)

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EP09177640 2009-12-01
EP10186537 2010-10-05
PCT/EP2010/068605 WO2011067272A1 (en) 2009-12-01 2010-12-01 Insecticidal compounds based on isoxazoline derivatives

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