DK2114885T3 - Fremgangsmåde til oxidation af bestemte substituerede sulfiliminer til insekticide sulfoximiner - Google Patents

Fremgangsmåde til oxidation af bestemte substituerede sulfiliminer til insekticide sulfoximiner Download PDF

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Publication number
DK2114885T3
DK2114885T3 DK07750610.3T DK07750610T DK2114885T3 DK 2114885 T3 DK2114885 T3 DK 2114885T3 DK 07750610 T DK07750610 T DK 07750610T DK 2114885 T3 DK2114885 T3 DK 2114885T3
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Denmark
Prior art keywords
alkyl
alkenyl
alkynyl
haloalkyl
alkoxy
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DK07750610.3T
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English (en)
Inventor
Kim E Arndt
Douglas C Bland
David E Podhorez
James R Mcconnell
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Dow Agrosciences Llc
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Publication of DK2114885T3 publication Critical patent/DK2114885T3/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C07D213/34—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (8)

1. Fremgangsmåde til fremstilling af insekticide sulfoximiner (la),
hvor Het betegner:
X betegner halogen, (Ci-C4)-alkyl, (Ci-C4)-halogenalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-halogenalkenyl, (Ci-C4)-alkoxy, (Ci-C4)-halogenalkoxy, CN, NO2, SOmR6, hvor m er et heltal fra 0-2, COOR4 eller CONR4R5; Y betegner hydrogen, halogen, (Ci-C4)-alkyl, (Ci-C4)-halogenalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-halogenalkenyl, (Ci-C4)-alkoxy, (Ci-C4)-halo-genalkoxy, CN, NO2, SOmR1, hvor m er et heltal fra 0-2, COOR4, CONR4R5, aryl eller heteroaryl; n er et heltal fra 0-3; L betegner enten en enkeltbinding, -CH(CH2)P-, hvor R1, S og L taget sammen betegner en 4-, 5- eller 6-leddet ring, og p er et heltal fra 1-3, -CH(CH20-CH2)-, hvor R1, S og L taget sammen betegner en 6-leddet ring, eller -CH-, hvor L, R2 og det fælles carbonatom, hvortil de er bundet, taget sammen betegner en 4-, 5- eller 6-leddet ring med op til, men ikke mere end, 1 heteratom; R1 betegner (Ci-C4)-alkyl, (Ci-C4)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-al-kynyl, (C3-C6)-halogenalkenyl, arylalkyl, heteroarylalkyl eller -CH2-, i tilfælde hvor R1, S og L taget sammen betegner en 4-, 5- eller 6-leddet ring; R2 og R3 uafhængigt betegner hydrogen, halogen, (Ci-C4)-alkyl, (Ci-C4)-ha-logenalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-halogenalkenyl, (C2-C4)-al-koxy, (Ci-C4)-halogenalkoxy, CN, SOmR6, hvor m er et heltal fra 0-2, COOR4, CONR4R5, arylalkyl, heteroarylalkyl, eller R2 og R3 og det fælles carbonatom, hvortil de er bundet, udgør en 3-6-leddet ring; R4 og R5 uafhængigt betegner hydrogen, (Ci-C4)-alkyl, (Ci-C4)-halogenalkyl; (C3-C6)-alkenyl, (C3-C6)-alkynyl, (C3-C6)-halogenalkenyl, aryl, heteroaryl, arylalkyl eller heteroarylalkyl; og R6 betegner (Ci-C4)-alkyl, (Ci-C4)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-al-kynyl, (C3-C6)-halogenalkenyl, arylalkyl eller heteroarylalkyl; og hvor "alkyl", "alkenyl", "alkynyl" og "alkoxy" indbefatter ligekædede, forgrenede og cykliske dele, og hver kan være usubstitueret eller substitueret med en eller flere substituenter valgt blandt, men ikke begrænset til halogen, hydroxy, alkoxy, alkylthio, (Ci-Ce)-acyl, formyl, cyano, aryloxy og aryl, forudsat at substitu-enterne er sterisk kompatible, og at reglerne for kemisk binding og spændingsenergi overholdes, og "aryl" henviser til en phenyl-, indanyl- eller naphthylgruppe; og "aryl" og "heteroaryl" kan være usubstitueret eller substitueret med en eller flere substituenter valgt blandt halogen, hydroxy, nitro, cyano, aryloxy, formyl, (Ci-Ce)-alkyl, (C2-C6)-alkenyl, (C2-Ce)-alkynyl, (Ci-Ce)-alkoxy, halogeneret (C1-Ce)-alkyl, halogeneret (C-i-CeJ-alkoxy, (C-i-CeJ-acyl, (Ci-Ce)-alkylthio, (Ci-Ce)-al-kylsulfinyl, (Ci-Ce)-alkylsulfonyl, aryl, (Ci-C6)-0C(0)alkyl, (Ci-C6)-NHC(0)alkyl, C(0)0H, (Ci-Ce)-C(0)Oalkyl, C(0)NH2, (Ci-Ce)-C(0)NHalkyl og (Ci-Ce)-C(0)N(alkyl)2, forudsat at substituenterne er sterisk kompatible, og at reglerne for kemisk binding og spændingsenergi overholdes; hvilken fremgangsmåde omfatter oxidation af en sulfilimin med formlen (I)
hvor R1, R2, R3, L, Het og n er som tidligere defineret, ved at bringe sulfiliminen i kontakt med et oxidationsmiddel, som omfatter et alkalimetalpermanganat, i et egnet organisk opløsningsmiddel, som er i det væsentlige inert over for de stærkt oxiderende betingelser, ved en temperatur fra -10 til 45°C.
2. Fremgangsmåde ifølge krav 1, hvor Het er (6-substitueret)pyridin-3-yl eller (2-substitueret)thiazol-5-yl, og hvor X er halogen eller (Ci-C2)-halogenalkyl, og Y er hydrogen.
3. Fremgangsmåde ifølge krav 1, hvor udgangssulfiliminen har strukturen
hvor Het, R2 og R3 er som tidligere defineret.
4. Fremgangsmåde ifølge krav 1, hvor udgangssulfiliminen har strukturen
hvor p er et heltal fra 1-3, og Het, R2 og R3 er som tidligere defineret.
5. Fremgangsmåde ifølge krav 1, hvor udgangssulfiliminen har strukturen
hvor p er et heltal fra 1 -3, og Het er som tidligere defineret.
6. Fremgangsmåde ifølge krav 1, hvor temperaturen er fra 10 til 30°C.
7. Fremgangsmåde ifølge krav 1, hvor det organiske opløsningsmiddel er et halogeneret alifatisk eller halogeneret aromatisk carbonhydrid eller et alifatisk eller aromatisk nitril.
8. Fremgangsmåde ifølge krav 1, hvor fremgangsmåden gennemføres i et tofaset opløsningsmiddelsystem, som omfatter en blanding af et halogeneret alifatisk carbonhydrid og vand.
DK07750610.3T 2007-02-09 2007-02-09 Fremgangsmåde til oxidation af bestemte substituerede sulfiliminer til insekticide sulfoximiner DK2114885T3 (da)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2007/003783 WO2008097235A1 (en) 2007-02-09 2007-02-09 Process for the oxidation of certain substituted sulfilimines to insecticidal sulfoximines

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EP (1) EP2114885B1 (da)
JP (1) JP5254999B2 (da)
KR (1) KR101379070B1 (da)
CN (1) CN101605760B (da)
AU (1) AU2007346136B2 (da)
BR (1) BRPI0721218A2 (da)
CA (1) CA2676700C (da)
DK (1) DK2114885T3 (da)
ES (1) ES2561355T3 (da)
HK (1) HK1139151A1 (da)
IL (1) IL199938A (da)
MX (1) MX2009008421A (da)
PL (1) PL2114885T3 (da)
WO (1) WO2008097235A1 (da)

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BR112023025278A2 (pt) 2021-06-02 2024-02-27 Syngenta Crop Protection Ag Derivados heterocíclicos com substituintes contendo sulfoximina ativos em termos pesticidas
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JP5254999B2 (ja) 2013-08-07
JP2010518078A (ja) 2010-05-27
MX2009008421A (es) 2009-11-02
AU2007346136A1 (en) 2008-08-14
BRPI0721218A2 (pt) 2013-01-01
IL199938A (en) 2015-05-31
PL2114885T3 (pl) 2016-07-29
ES2561355T3 (es) 2016-02-25
CN101605760B (zh) 2012-06-20
KR101379070B1 (ko) 2014-03-28
EP2114885A1 (en) 2009-11-11
HK1139151A1 (en) 2010-09-10
KR20100014384A (ko) 2010-02-10
WO2008097235A1 (en) 2008-08-14
CA2676700A1 (en) 2008-08-14
AU2007346136B2 (en) 2012-10-25
EP2114885B1 (en) 2016-01-27
CN101605760A (zh) 2009-12-16
IL199938A0 (en) 2010-04-15
CA2676700C (en) 2013-12-17

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